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Cas Database

591-78-6

591-78-6

Identification

  • Product Name:2-Hexanone

  • CAS Number: 591-78-6

  • EINECS:209-731-1

  • Molecular Weight:100.161

  • Molecular Formula: C6H12O

  • HS Code:2914.19 Oral rat LD50: 2590 mg/kg

  • Mol File:591-78-6.mol

Synonyms:2-Oxohexane;Butyl methyl ketone;MBK;Methyl butyl ketone;Methyl n-butyl ketone;n-Butylmethyl ketone;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT

  • Hazard Codes: T:Toxic;

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH336 May cause drowsiness or dizziness

  • 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 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. Do NOT induce vomiting. Refer for medical attention . Inhalation of high concentrations of vapor may result in narcosis; peripheral neuropathy may develop. Ingestion of large amounts may cause some systemic injury. Contact with eyes causes mild to moderate irritation. Liquid irritates skin; prolonged or repeated contact may cause defatting of the skin with resultant dermatitis. (USCG, 1999) An accurate history is essential to determine whether a person has been exposed to /2-hexanone/. ...Patient may report weakness, muscle cramps, numbness, and paresthesias such as the feeling of tingling, burning, and freezing. Impotence may occur. The physical examination should examine all muscle groups for weakness. Peripheral muscles are affected first, with more proximal weakness after more prolonged exposure. Muscle stretch reflexes are absent distally in areas of weakness. Atrophy of the hand muscles has been reported. Hyperhidrosis may occur. All sensory modalities may be affected, including touch and proprioception. Patients should be assessed for cerebellar signs and tremor. Visual acuity and peripheral vision changes have not been reported, whereas blurred vision has. Tinnitus may occur. Signs of parkinsonism should be sought. ...The patient must be removed from all future exposure. Physical therapy should be initiated to maintain full range of motion until reinnervation occurs. Recovery is slow, as the regeneration of axon fibers must take place. Complete recovery of strength may not occur.

  • Fire-fighting measures: Suitable extinguishing media If material is on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. This chemical is flammable. 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. 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. Environmental considerations -- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bangs, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.

  • 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.MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ...

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 1 ppm (4 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 339 Articles be found

Investigation of the Wacker Process in Formamide Microemulsions

Rico, I.,Couderc, F.,Perez, E.,Laval, J. P.,Lattes, A.

, p. 1205 - 1206 (1987)

Formamide microemulsions have been used as reaction media for the Wacker process, giving much faster oxidation of hex-1-ene to hexan-2-one than in classical media.

Rh(I)-Cu(II) Catalyzed Oxidation of 1-Hexene by O2 Using Immobilized, Site-Separated Organosulfide Complexes

Nyberg, Eric D.,Drago, Russell S.

, p. 4966 - 4968 (1981)

-

Specific Oxidation of 2 by O2 via the Coordination of in Situ Generated HOOH. Implications for the Rh(III)/Cu(II)-Catalyzed O2 Oxidation of 1-Alkenes to 2-Ketones

Nyberg, Eric D.,Pribich, David C.,Drago, Russell S.

, p. 3538 - 3544 (1983)

The oxidation of 1-hexene to 2-hexanone catalyzed by Rh(III)/Cu(II) mixtures is investigated.In order to study the reactions that rhodium undergoes to form an active catalyst, 2 (A) is used as a catalyst precursor.A number of results are obtained that indicate that this species must be converted to a rhodium(III) complex before catalysis occurs.With A as a catalyst precursor in the absence of Cu(II), long induction are observed for catalytic oxidations.Rhodium(I) is oxidized to rhodium(III) chloride during the induction period.Furthermore, at higher chloride/rhodium ratios (up to a 10:1 mole ratio), greater initial rates and catalyst stabilities are found.These observations are used as partial justification for characterizing rhodium(III) as an active catalyst in the oxidation of 1-hexene to 2-hexanone.The oxidation of 2 to rhodium(III) chloride is investigated in detail.An unusual mechanism for this reaction is proposed.Hydrogen peroxide, produced in situ from the reduction of O2 by alcohol solvent, oxidizes 2.An intermediate hydroperoxide complex is formed in the course of the oxidation to rhodium(III) which contains a coordinated carbonyl ligand (B).This intermediate is studied in dilute solution and is found to decompose immediately when attempts are made to isolate it.Very few stable hydroxyperoxide and alkylperoxide complexes of the platinum metals have been reported; some are capable of oxidizing terminal olefins to 2-ketones.In contrast, the oxidation of 2 to rhodium(III) chloride under identical conditions is much faster and proceeds by a mechanism avoiding detectable quantities of this hydroperoxo intermediate, while 2 is not oxidized even after 48 h.The oxidation of A to B occurs only in solvents capable of reducing O2.

-

Daschkewitsch

, (1948)

-

New insight into the mechanism of the reaction between α,β-unsaturated carbonyl compounds and triethylborane (Brown's reaction)

Beraud, Valérie,Gnanou, Yves,Walton, John C.,Maillard, Bernard

, p. 1195 - 1198 (2000)

A study of the reaction of α,β-unsaturated carbonyl compounds with triethylborane under free radical conditions (Brown's reaction) including spectroscopic analyses (11B NMR, IR, EPR) of products and intermediates indicated that these reactions involve the prior formation of an 'α,β- unsaturated carbonyl compound-organoborane' complex. (C) 2000 Elsevier Science Ltd.

Activation of Molecular Hydrogen and Oxygen by PSiP Complexes of Cobalt

Murphy, Luke J.,Ruddy, Adam J.,McDonald, Robert,Ferguson, Michael J.,Turculet, Laura

, p. 4481 - 4493 (2018)

The syntheses of CoII halide complexes supported by κ3-(2-Cy2PC6H4)2SiMe (Cy-PSiP) ligation are detailed. Reduction of (Cy-PSiP)Co(PMe3)I could be achieved under mild conditions using magnesium metal to generate the CoI complex (Cy-PSiP)Co(PMe3)N2 in high yield. When this reaction was carried out under an atmosphere of CO, (Cy-PSiP)Co(CO)2 was obtained. Unlike the facile reduction of CoII to CoI, attempts to access CoIII species supported by Cy-PSiP ligation proved challenging. Attempted oxidative addition reactions involving (Cy-PSiP)Co(PMe3)N2 were generally unsuccessful, with the sole exception of H2, which reacted to afford the dihydride complex (Cy-PSiP)Co(PMe3)(H)2. The dihydride complex undergoes Co-H site exchange in solution and readily eliminates H2. The CoI precursor (Cy-PSiP)Co(PMe3)N2 is a competent precatalyst for the hydrogenation of terminal alkenes. Exposure of (Cy-PSiP)CoI to O2 gas under anhydrous conditions led to rapid ligand oxidation at Si and P, with no evidence observed at low temperature for a CoIII superoxo or peroxo intermediate. Exclusive oxidation at Si to afford a CoII-siloxy complex was observed upon treatment of (Cy-PSiP)CoI with one equiv. Me3NO. While this siloxy complex did not react further with O2, treatment with a second equiv. of Me3NO led to subsequent oxidation involving one phosphino donor. This observation supports the notion that in the ligand oxidation reactivity observed with O2, the O atoms incorporated at both Si and P are likely derived from the same O2 molecule.

Mechanisms for High Selectivity in the Hydrodeoxygenation of 5-Hydroxymethylfurfural over PtCo Nanocrystals

Luo, Jing,Yun, Hongseok,Mironenko, Alexander V.,Goulas, Konstantinos,Lee, Jennifer D.,Monai, Matteo,Wang, Cong,Vorotnikov, Vassili,Murray, Christopher B.,Vlachos, Dionisios G.,Fornasiero, Paolo,Gorte, Raymond J.

, p. 4095 - 4104 (2016)

Carbon-supported, Pt and PtCo nanocrystals (NCs) with controlled size and composition were synthesized and examined for hydrodeoxygenation (HDO) of 5-hydroxymethylfurfural (HMF). Experiments in a continuous flow reactor with 1-propanol solvent, at 120 to 160 °C and 33 bar H2, demonstrated that reaction is sequential on both Pt and PtCo alloys, with 2,5-dimethylfuran (DMF) formed as an intermediate product. However, the reaction of DMF is greatly suppressed on the alloys, such that a Pt3Co2 catalyst achieved DMF yields as high as 98%. XRD and XAS data indicate that the Pt3Co2 catalyst consists of a Pt-rich core and a Co oxide surface monolayer whose structure differs substantially from that of bulk Co oxide. Density functional theory (DFT) calculations reveal that the oxide monolayer interacts weakly with the furan ring to prevent side reactions, including overhydrogenation and ring opening, while providing sites for effective HDO to the desired product, DMF. We demonstrate that control over metal nanoparticle size and composition, along with operating conditions, is crucial to achieving good performance and stability. Implications of this mechanism for other reactions and catalysts are discussed.

Selective oxidation of n-hexane by Cu (II) nanoclusters supported on nanocrystalline zirconia catalyst

Acharyya, Shankha Shubhra,Ghosh, Shilpi,Adak, Shubhadeep,Singh, Raghuvir,Saran, Sandeep,Bal, Rajaram

, p. 5816 - 5822 (2015)

Cu (II) nanoclusters supported on nanocrystalline zirconia catalyst (with size ~15 nm), was prepared by using cationic surfactant cetyltrimethylammonium in a hydrothermal synthesis method. The catalyst was characterized by XRD, XPS, TGA, SEM, TEM, FTIR and ICP-AES. The catalyst was found to be efficient in selective oxidation of n-hexane to 2-hexanol. An n-hexane conversion of 55%, with a 2-hexanol selectivity of 70% was achieved over this catalyst in liquid phase, without the use of any solvent. The catalyst can be reused several times without any significant activity loss.

Synthesis and Reactivity of Cobalt(I) and Iridium(I) Complexes Bearing a Pentadentate N-Homoallyl-Substituted Bis(NHC) Pincer Ligand

Tian, Yingying,Maulbetsch, Theo,Jordan, Ronja,T?rnroos, Karl W.,Kunz, Doris

, p. 1221 - 1229 (2020)

Two methods for the synthesis of the bis(imidazolin-2-ylidene)carbazolide cobalt(I) complex [Co(bimcaHomo)] (2) have been developed. The first route relies on the direct transmetalation of the in situ generated lithium complex [Li(bimcaHomo)] with CoCl(PPh3)3. The second route is a two-step synthesis that consists of the transmetalation of [Li(bimcaHomo)] with CoCl2 followed by reduction of the Co(II) complex to yield the desired Co(I) complex 2. The analogous iridium complex [Ir(bimcaHomo)] (4) was prepared by transmetalation of [Li(bimcaHomo)] or [K(bimcaHomo)] with [Ir(μ-Cl)(COD)]2. The catalytic activity of complexes 2 and 4 in the epoxide isomerization was tested in the absence and presence of H2. When [M(bimcaHomo)] (M = Ir (4), Rh (3)) was exposed to 1 bar of H2 at 80 °C, single crystals formed whose X-ray structure analyses revealed the hydrogenation of the N-homoallyl moieties and formation of the dimeric hydrido complexes [Ir(bimcan-Bu)(H)2]2 (7) and [Rh(bimcan-Bu)(H)2]2 (8).

Experimental and theoretical study of gold(III)-catalyzed hydration of alkynes

Cordon, Jesus,Jimenez-Oses, Gonzalo,Lopez-De-Luzuriaga, Jose M.,Monge, Miguel,Olmos, M. Elena,Pascual, David

, p. 3823 - 3830 (2014)

The properties of different Au(III) halo dithiocarbamate complexes of structure [AuX2(S2CN(R)2)] as suitable catalysts for the hydration reaction of phenylacetylene have been tested. Moderate catalytic activity was found for X = Cl, Br, while those compounds in which X = I, C6F5 are inert. A working mechanism involving the initial dissociation of a labile ligand (Cl or Br) followed by coordination and activation of the alkyne, solvent-assisted attack of water, and enol tautomerization has been proposed through computational studies.

Wacker-type oxidation in vapor phase using a palladium-copper chloride catalyst in a liquid polymer medium supported on silica gel

Okamoto, Masaki,Taniguchi, Yuichi

, p. 195 - 200 (2009)

Pd(II) chloride and Cu(II) chloride in various liquid polymer media supported on silica gel were prepared and used in a catalyst system for vapor-phase synthesis of acetaldehyde by Wacker-type oxidation of ethylene. This catalyst system supported on silica gel prepared by impregnation was quickly deactivated, while use of polyethylene glycol (PEG) as a liquid polymer medium supported on silica gel showed stable catalytic activity. PEG inhibited the formation of Pd metal particles, which deactivate the catalyst system. Addition of alkali metal salts, especially LiCl, to the PdCl2-CuCl2 catalyst system with PEG enhanced catalytic activity for 22 h, even when the Pd content was high, leading to high activity but poor stability. LiCl also inhibited the formation of metal particles.

High-throughput measurement of the enantiomeric excess of chiral alcohols by using two enzymes

Li, Zhi,Buetikofer, Lukas,Witholt, Bernard

, p. 1698 - 1702 (2004)

Rapid ee determination: Enantioselective alcohol dehydrogenases A and B were used to oxidize chiral alcohols in a sensitive, accurate, high-throughput method (see scheme). The reaction rates were determined by monitoring the formation of NAD(P)H by UV spectroscopy. The ee value was calculated from the reaction rates and the kinetic constants of the enzymes.

Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor

Luo, Jing,Arroyo-Ramírez, Lisandra,Wei, Jifeng,Yun, Hongseok,Murray, Christopher B.,Gorte, Raymond J.

, p. 86 - 93 (2015)

The three-phase hydrodeoxygenation (HDO) of 5-hydroxymethylfurfural (HMF) and hydrogenation of 2,5-dimethylfuran (DMF) were studied over six carbon-supported metal catalysts (Pt, Pd, Ir, Ru, Ni, and Co) using a tubular flow reactor with 1-propanol solvent, at 180 °C and 33 bar. By varying the space time in the reactor, the reaction of HMF is shown to be sequential, with HMF reacting first to furfuryl ethers and other partially hydrogenated products, which then form 2,5-dimethylfuran (DMF). Ring-opened products and 2,5-dimethyltetrahydrofuran (DMTHF) were produced only from reaction of DMF. Rate constants for the pseudo-first-order sequential reactions were obtained for each of the metals. The selectivities for the reaction of DMF varied with the metal catalyst, with Pd forming primarily DMTHF, Ir forming a mixture of DMTHF and open-ring products, and the other metals forming primarily open-ring products. Catalyst stabilities followed the order Pt ~ Ir > Pd > Ni > Co > Ru. Since the stability order correlated with carbon balances in the product (>93% for Pt; 75% for Ru), deactivation appears to be caused by deposition of humins on the catalyst.

Chromium-Catalyzed Production of Diols From Olefins

-

Paragraph 0111, (2021/03/19)

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Synthesis of TS-1 zeolites from a polymer containing titanium and silicon

Xing, Jiacheng,Yuan, Danhua,Liu, Hanbang,Tong, Yansi,Xu, Yunpeng,Liu, Zhongmin

, p. 6205 - 6213 (2021/03/22)

The synthesis of TS-1 zeolites is regarded as a milestone in zeolite history, and it has led to the revolution of the green oxidation system of using H2O2as an oxidant, leaving only water as the byproduct. However, because of the highly hydrolyzable titanium source, the preparation of TS-1 requires complex synthesis conditions. Moreover, the difference in the hydrolysis rate between the silicon source and titanium source tends to increase the difficulty of titanium insertion into the framework, and it is easy to generate extra-framework Ti species during the synthesis. Here, a high-quality TS-1 zeolite with a large external surface area and free of extra-framework Ti species has been successfully synthesized by using a kind of novel polymer containing titanium and silicon. Due to the high hydrolysis resistance of the polymer reagent, a good matching of the hydrolysis rate between the silicon source and the titanium source is realized during crystallization, which facilitates the incorporation of titanium into the framework. Furthermore, the TS-1 zeolite exhibited excellent catalytic performance inn-hexane oxidation with hydrogen peroxide as the oxidant. This method of synthesizing zeolites from polymers is expected to be widely applied for the synthesis of other titanium-containing zeotype materials.

Boosting homogeneous chemoselective hydrogenation of olefins mediated by a bis(silylenyl)terphenyl-nickel(0) pre-catalyst

Lücke, Marcel-Philip,Yao, Shenglai,Driess, Matthias

, p. 2909 - 2915 (2021/03/14)

The isolable chelating bis(N-heterocyclic silylenyl)-substituted terphenyl ligand [SiII(Terp)SiII] as well as its bis(phosphine) analogue [PIII(Terp)PIII] have been synthesised and fully characterised. Their reaction with Ni(cod)2(cod = cycloocta-1,5-diene) affords the corresponding 16 VE nickel(0) complexes with an intramolecularη2-arene coordination of Ni, [E(Terp)E]Ni(η2-arene) (E = PIII, SiII; arene = phenylene spacer). Due to a strong cooperativity of the Si and Ni sites in H2activation and H atom transfer, [SiII(Terp)SiII]Ni(η2-arene) mediates very effectively and chemoselectively the homogeneously catalysed hydrogenation of olefins bearing functional groups at 1 bar H2pressure and room temperature; in contrast, the bis(phosphine) analogous complex shows only poor activity. Catalytic and stoichiometric experiments revealed the important role of the η2-coordination of the Ni(0) site by the intramolecular phenylene with respect to the hydrogenation activity of [SiII(Terp)SiII]Ni(η2-arene). The mechanism has been established by kinetic measurements, including kinetic isotope effect (KIE) and Hammet-plot correlation. With this system, the currently highest performance of a homogeneous nickel-based hydrogenation catalyst of olefins (TON = 9800, TOF = 6800 h?1) could be realised.

Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst

Klarner, Mara,Bieger, Sandra,Drechsler, Markus,Kempe, Rhett

supporting information, p. 2157 - 2161 (2021/05/21)

The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.

Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst

Beller, Matthias,Feng, Lu,Gao, Jie,Jackstell, Ralf,Jagadeesh, Rajenahally V.,Liu, Yuefeng,Ma, Rui

supporting information, p. 18591 - 18598 (2021/06/28)

A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.

Process route upstream and downstream products

Process route

hypochlorous acid 1-methyl-pentyl ester
40137-10-8

hypochlorous acid 1-methyl-pentyl ester

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

n-hexan-2-ol
626-93-7

n-hexan-2-ol

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

n-hexan-2-one

5-chlorohexan-2-ol
52355-86-9

5-chlorohexan-2-ol

Conditions
Conditions Yield
With sodium hydrogencarbonate; iron(II) sulfate; In tetrachloromethane; Ambient temperature; protected from the light;
71%
7%
8%
D-sorbitol
50-70-4

D-sorbitol

TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

methanol
67-56-1

methanol

propan-1-ol
71-23-8

propan-1-ol

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

3-methyl-cyclopentanone
1757-42-2,6195-92-2

3-methyl-cyclopentanone

propylene glycol
57-55-6,63625-56-9

propylene glycol

ethanol
64-17-5

ethanol

n-hexan-3-ol
623-37-0

n-hexan-3-ol

2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

(S)-Ethyl lactate
687-47-8

(S)-Ethyl lactate

pentan-1-ol
71-41-0

pentan-1-ol

vinyl formate
692-45-5

vinyl formate

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

n-hexan-2-one

n-hexan-3-one
589-38-8

n-hexan-3-one

Isopropyl acetate
108-21-4

Isopropyl acetate

3-Hydroxy-2-pentanone
3142-66-3,113919-08-7

3-Hydroxy-2-pentanone

acetic acid
64-19-7,77671-22-8

acetic acid

propionaldehyde
123-38-6

propionaldehyde

2-Pentanone
107-87-9

2-Pentanone

propionic acid
802294-64-0,79-09-4

propionic acid

1-Hydroxy-2-butanone
5077-67-8

1-Hydroxy-2-butanone

2,5-hexanedione
110-13-4

2,5-hexanedione

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

isopropyl alcohol

acetone
67-64-1

acetone

pentan-3-one
96-22-0

pentan-3-one

isobutyric Acid
79-31-2

isobutyric Acid

butanone
78-93-3

butanone

iso-butanol
78-92-2,15892-23-6

iso-butanol

hexanoic acid
142-62-1

hexanoic acid

Isosorbide
652-67-5

Isosorbide

butyric acid
107-92-6

butyric acid

2.3-butanediol
513-85-9

2.3-butanediol

hexan-1-ol
111-27-3

hexan-1-ol

valeric acid
109-52-4

valeric acid

Conditions
Conditions Yield
platinum on carbon; In water; for 3h; Direct aqueous phase reforming;
dibenzofuran
132-64-9,214827-48-2

dibenzofuran

cyclohexenone
930-68-7

cyclohexenone

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

diphenylether
101-84-8

diphenylether

tert-butylbenzene
253185-03-4,253185-04-5

tert-butylbenzene

propane
74-98-6

propane

hexane
110-54-3

hexane

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

n-hexan-2-one

2-methyl-2-cyclopenten-1-one
1120-73-6

2-methyl-2-cyclopenten-1-one

n-pentylcyclohexane
4292-92-6

n-pentylcyclohexane

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

1-butylbenzene
104-51-8

1-butylbenzene

pentylbenzene
538-68-1

pentylbenzene

cyclopentylbenzene
700-88-9

cyclopentylbenzene

4-Phenylphenol
92-69-3

4-Phenylphenol

dicyclohexyl ether
4645-15-2

dicyclohexyl ether

2-phenylpentane
2719-52-0

2-phenylpentane

1-pentenylbenzene
826-18-6

1-pentenylbenzene

2-butylcyclohexanone
1126-18-7

2-butylcyclohexanone

cyclohexylphenyl ether
2206-38-4

cyclohexylphenyl ether

2-cyclohexylphenol
119-42-6

2-cyclohexylphenol

3-methyl-phenol
108-39-4

3-methyl-phenol

ortho-cresol
95-48-7,77504-84-8

ortho-cresol

2-Phenylphenol
90-43-7,287950-96-3

2-Phenylphenol

cyclohexene
110-83-8

cyclohexene

cyclohexanol
108-93-0

cyclohexanol

Conditions
Conditions Yield
With hydrogen; 1 wtpercent K/1 wtpercent Pt/SiO2; at 425 ℃; under 5931.67 Torr;
2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

n-hexan-2-ol
626-93-7

n-hexan-2-ol

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

n-hexan-2-one

Conditions
Conditions Yield
With platinum on activated charcoal; at 95 ℃; Temperature; Catalytic behavior;
With hydrogen; In cyclohexane; at 120 ℃; under 45004.5 Torr; Reagent/catalyst; Catalytic behavior;
With cesium 12-tungstophosphate; hydrogen; In decane; at 90 ℃; for 2h; under 15001.5 Torr; Autoclave; Green chemistry;
45 %Chromat.
20 %Chromat.
20 %Chromat.
2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

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

n-hexan-2-one

Conditions
Conditions Yield
With palladium on activated charcoal; at 220 ℃; Reagent/catalyst;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 175 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water; 1,4-dioxane / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In 1,4-dioxane; water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water; 1,4-dioxane / 16 h / 175 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In 1,4-dioxane; water;
With hydrogen; at 200 ℃; for 7.22222E-05h; Temperature; Reagent/catalyst; Kinetics;
2,5-hexanedione
110-13-4

2,5-hexanedione

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

hexane
110-54-3

hexane

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

n-hexan-2-one

Conditions
Conditions Yield
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water; at 200 ℃; for 16h; under 41254.1 Torr; Autoclave; Sealed tube;
33 %Chromat.
9 %Chromat.
9 %Chromat.
With hydrogen; In pentane; at 200 ℃; for 1h; under 10351 Torr;
2,5-hexanedione
110-13-4

2,5-hexanedione

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

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

n-hexan-2-one

Conditions
Conditions Yield
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water; at 225 ℃; for 16h; under 41254.1 Torr; Autoclave; Sealed tube;
7 %Chromat.
12 %Chromat.
2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

hexane
110-54-3

hexane

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

n-hexan-2-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 175 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water; 1,4-dioxane / 16 h / 225 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In 1,4-dioxane; water;
Multi-step reaction with 2 steps
1: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen / water; 1,4-dioxane / 16 h / 175 °C / 41254.1 Torr / Autoclave; Sealed tube
2: [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; trifluorormethanesulfonic acid; hydrogen / water / 16 h / 200 °C / 41254.1 Torr / Autoclave; Sealed tube
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In 1,4-dioxane; water;
With cesium 12-tungstophosphate; 1% platinum on alumina; hydrogen; at 70 ℃; for 1h; Temperature; Reagent/catalyst; Catalytic behavior; Flow reactor; Green chemistry;
16.8 %Chromat.
10.9 %Chromat.
64.5 %Chromat.
With cesium 12-tungstophosphate; hydrogen; at 70 ℃; for 1h; Reagent/catalyst; Temperature; Catalytic behavior; Flow reactor; Green chemistry;
46.5 %Chromat.
16 %Chromat.
35.8 %Chromat.
2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

hexane
110-54-3

hexane

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

n-hexan-2-one

2,5-hexanedione
110-13-4

2,5-hexanedione

Conditions
Conditions Yield
With trifluorormethanesulfonic acid; [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In 1,4-dioxane; water; at 225 ℃; for 16h; under 41254.1 Torr; Autoclave; Sealed tube;
26 %Chromat.
19 %Chromat.
10 %Chromat.
5 %Chromat.
2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

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

n-hexan-2-one

2,5-hexanedione
110-13-4

2,5-hexanedione

Conditions
Conditions Yield
With [(4′-Ph-2,2′:6′,2″-terpyridine)Ru-(H2O)3](trifluoromethanesulfonate)2; hydrogen; In water; at 225 ℃; for 16h; under 41254.1 Torr; Autoclave; Sealed tube;
16 %Chromat.
40 %Chromat.
8 %Chromat.

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