34363-01-4

Usage

Chemical Properties

generally provided as an aqueous emulsion (ca. 30%)

Upstream product

• 499-69-4 (+/-)-menthol 
• 74233-53-7 1-p-menthanyl chloride 
• 3901-93-7 1-methyl-4-(1-methylethyl)cyclohexanol 
• 5989-27-5 D-limonene 
• 952207-04-4 H-menthyl phosphonate 
• 138-86-3 limonene. 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 1195-31-9 (+)-p-menth-1-ene 
• 99-83-2 p-mentha-1,5-diene 
• 95-49-8 2-methylchlorobenzene 
• 5113-93-9 (1R)-trans-p-menth-2-ene 
• 64-17-5 ethanol 
• 2216-54-8 L-menthylamine 
• 64-19-7 acetic acid 

Downstream Products

• 101448-24-2 Diacetat des 1,2-Bis-hydroxymethyl-p-menthens-⁽⁵⁾ 
• 110851-26-8 2-Iodo-4-isopropenyl-1-methyl-cyclohexane 
• 74233-53-7 1-p-menthanyl chloride 
• 51795-53-0 (2S,5R)-(+)-2-chloro-2-methyl-5-isopropylcyclohexanone 
• 84098-59-9 5-(2,2-Dichloro-ethyl)-6-methyl-heptan-2-one 
• 80324-58-9 3-Chloro-5-(2-chloro-ethyl)-6-methyl-heptan-2-one 
• 1020401-13-1 (1S,2S,5R,6R,7S)-2-isopropyl-5-methyl-bicyclo[4.1.0]heptane-7-carboxylic acid ethylamide 
• 1020401-11-9 (1R,2S,5R,6S,7R)-2-isopropyl-5-methyl-bicyclo[4.1.0]heptane-7-carboxylic acid ethylamide 
• 131246-71-4 4-methyl-N-(1-p-menthen-10-yl)benzenesulfonamide 
• 131321-62-5 N-trans-[5-isopropyl-2-methylcyclohex-2-enyl]toluenosulfonamide 
• 90582-69-7 N-[trans-5-isopropyl-2-methylcyclohex-2-enyl]amine 
• 99175-00-5 (1S,2S,4R)-1-hydroxy-p-menthan-2-ylmercury ⁽¹⁺⁾; chloride 
• 103983-73-9 (5-Isopropyl-2-methylene-cyclohexyl)-methanol 
• 6007-05-2 (5-Isopropyl-2-methyl-cyclohex-1-enyl)-methanol 

Relevant academic research and scientific papers

Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.

[reaction: see text] A concise asymmetric synthesis of the tricyclic core of cyathane diterpenes is described, based on a novel transition-metal-catalyzed intramolecular [5 + 2] cycloaddition of ynone-vinylcyclopropane 10 (assembled from commercially avai

Magnesium activation of dichlorodi-η5-cyclopentadienyltitanium in the catalytic hydrogenation of olefins and acetylenes

Magnesium activation of dichlorodi-η5-cyclopentadienyltitanium (Cp2TiCl2) in tetrahydrofuran (THF) under a dihydrogen atmosphere has been shown to produce a stable solution which effectively hydrogenates various types of olefins and acetylenes

Continuous production of the renewable ρ-cymene from α-pinene

The aim of this work was to demonstrate the feasibility to produce ρ-cymene, an important commodity chemical, in a continuous, one-pot reaction system from abundant α-pinene, available e.g. as a by-product of pulping industry. The isomerization reactions of α-pinene over bimetallic heterogeneous catalysts, 3 and 5 wt% Pd-Zn (1:1, 1:4, 4:1, 1:0, and 0:1), supported on Al-SBA15 were studied. The principal reaction products were identified as ρ- and m-cymenes, limonene, camphene, and ρ-menthene, respectively. The highest concentration of ρ-cymene reached 77 wt% under the optimized reaction conditions: 300 C and α-pinene feed of 0.03 mL/min. Two main reaction pathways toward ρ- and m-cymenes were described, and a mechanistic kinetic model, based on a plausible reaction network in line with Langmuir-Hinshelwood approach, was developed. The catalyst characterization revealed the reduction in Pd(II) sites, catalyst coking, and decline of surface area over the course of time. The catalyst recovery and reuse was addressed.

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

Remarkable catalytic activity of polymeric membranes containing gel-trapped palladium nanoparticles for hydrogenation reactions

Polymeric flat-sheet membranes and hollow fibers were prepared via UV photo-initiated polymerization of acrylic acid at the surface of commercial polyether sulfones (PES) membranes. These polymeric materials permitted to immobilize efficiently palladium nanoparticles (PdNP), which exhibited a mean diameter in the range of 4?6 nm. These materials were synthesized by chemical reduction of Pd(II) precursors in the presence of the corresponding support. We successfully applied the as-prepared catalytic materials in hydrogenation reactions under continuous flow conditions. Flat sheet membranes were more active than hollow fibers due to the flow configuration and defavorable operating conditions. Actually, various functional groups (i.e. C[dbnd]C, C[tbnd]C and NO2) were reduced in flow-through configuration, under mild conditions (between 1.4 and 2.2 bar H2 at 60 °C, using 3.2 mol% of Pd loading), archiving high conversions in short reaction times (12?24 s).

Method for synthesizing bark beetle pheromone

The bark beetle pheromone is (1S, 4R) -4 - isopropyl -1 - methyl -2 -cyclohexene -1 - alcohol, and the synthetic method comprises the following steps: forming a clathrate compound with (S)- (-) - limonene and carrying out catalytic hydrogenation reaction

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.

Photo-Initiated Cobalt-Catalyzed Radical Olefin Hydrogenation

Outer-sphere radical hydrogenation of olefins proceeds via stepwise hydrogen atom transfer (HAT) from transition metal hydride species to the substrate. Typical catalysts exhibit M?H bonds that are either too weak to efficiently activate H2 or too strong to reduce unactivated olefins. This contribution evaluates an alternative approach, that starts from a square-planar cobalt(II) hydride complex. Photoactivation results in Co?H bond homolysis. The three-coordinate cobalt(I) photoproduct binds H2 to give a dihydrogen complex, which is a strong hydrogen atom donor, enabling the stepwise hydrogenation of both styrenes and unactivated aliphatic olefins with H2 via HAT.

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

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.

Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.