535-77-3

Usage

Uses

M-CyMene is a pharmaceutical intermediate in laboratory R&D processes.

InChI:InChI=1/C10H14/c1-8(2)10-6-4-5-9(3)7-10/h4-8H,1-3H3

Upstream product

• 1072-16-8 2,7-dimethyloctane 
• 38738-60-2 carvestrene 
• 1195-79-5 1,3,3-trimethyl-2-norbornanone 
• 99-87-6 4-methylisopropylbenzene 
• 1124-20-5 2-(3-methylphenyl)propene 
• 5208-37-7 8-hydroxy-m-cymene 
• 76-22-2 Camphor 
• 498-15-7 (+)-Δ³-carene 
• 118-75-2 chloranil 
• 4497-92-1 2-carene 
• 75-30-9 2-iodo-propane 
• 108-88-3 toluene 
• 187737-37-7 propene 
• 98-82-8 Isopropylbenzene 

Downstream Products

• 408309-49-9 4-isopropyl-2-methyl-benzyl chloride 
• 29577-19-3 1-tert-butyl-3-isopropyl-5-methyl-benzene 
• 16580-24-8 1-isopropyl 3-methyl cyclohexane 
• 121-91-5 isophthalic acid 
• 859816-25-4 4-isopropyl-2-methyl-1-nitro-benzene 
• 36860-15-8 2,4-dichloro-3,5-dinitro-toluene 
• 51676-76-7 2,6-dichloro-3,5-dinitrotoluene 
• 99758-99-3 2-isopropyl-4-methyl-1,3,5-trinitro-benzene 
• 40912-34-3 3-(1-hydroxy-1-methylethyl)benzoic acid 
• 111849-62-8 1,3,3,5-tetramethyl-1-(3-tolyl)-2,3-dihydro-1H-indene 
• 108-39-4 3-methyl-phenol 
• 187737-37-7 propene 
• 108-88-3 toluene 
• 1202-08-0 2-methyl-5-isopropylacetophenone 

Relevant academic research and scientific papers

Solvent-free isomerization of 3-carene to 2-carene using Na/o-chlorotoluene catalyst in trans-isolimonene production

Trans-isolimonene is one of the important compound in drugs development. This compound can be made by isomerization of inexpensive 3-carene via 2-carene using Na/o-chlorotoluene catalyst in xylene. The existence of xylene as a solvent requires a further separation process that can reduce the efficiency when applied in the bulk industry. The isomerization of 3-carene to 2-carene has been studied in solvent free reaction compared by isomerization without xylene solvent. The result showed that the isomerization can also occur in solvent-free condition. Solventfree isomerization gave 27.72% of conversion and 83.27% of selectivity while isomerization with solvent gave 23.59% of conversion and 86.87% of selectivity.

Gas phase toluene isopropylation over high silica mordenite

Mordenite (HM) catalysts with three different Si/Al ratios were compared for their activity and selectivities in gas phase toluene isopropylation with isopropanol. Catalyst with Si/Al ratio 44·9 offered better cumene selectivity, hence, it was chosen for detailed kinetic investigations. The influence of various process parameters like temperature, time-on-stream, weight hourly space velocity (WHSV), reactant mole ratio on this catalyst activity are discussed. The cymene selectivity was found to increase with reaction temperature and passed through a maximum at 473 K. The deactivation with time-onstream is almost negligible. Lower isopropyl alcohol concentration in the feed improved cymene selectivity. The conversion and selectivity to cymenes were compared with those of the large pore beta catalyst. The rate constant and activation energy were found to be 7·34 m3/kg h and 41·84 kJ/mol, respectively using homogeneous kinetic model. Indian Academy of Sciences.

Alkylation of Toluene with Isopropanol on Lantanum Modified ZSM-5 Zeolite

Abstract: The effect of lanthanum concentration on the physicochemical and catalyticproperties of HZSM-5 zeolite in a reaction of toluene alkylation withisopropanol was studied in a temperature range of 250–350°C. Based on the dataobtained by X-ray diffraction analysis, low-temperature nitrogen adsorption (BETmethod), and IR spectroscopy, it was shown that an increase in lanthanumconcentration in HZSM-5 from 1.0 wt % to 7.0 wt % reduces both the specificsurface area and the pore volume of the zeolite despite the retention of itscrystalline structure. This also results in redistribution of acid sites,specifically decreases the concentration of strong Br?nsted acid sites (B) andincreases that of moderate Lewis acid sites (L), thus decreasing the B/L ratiofrom 3.53 to 0.20. All these occurrences have a crucial effect on theselectivity of reaction products and, in particular, on the p-isopropyl toluene (4-IPT) selectivity. Maximumselectivity, making up 72.4%, is achieved by a zeolite containing 5.0 wt %lanthanum at a B/L ratio of 0.25.

Novel approach towards Al-rich AFI for catalytic application

A new germanosilicate structural analogue of AFI zeolite (Ge-AFI) was hydrothermally synthesized. One- and two-step alumination of the Ge-AFI zeolites were used to modify their structure and acidic properties traced using XRD, N2 adsorption, ICP-OES, 27Al NMR, and FTIR spectroscopy. Two-step aluminated sample (deGe-Al-AFI) provided a higher Al content, stronger acid sites and a higher micropore volume than one-step aluminated sample (Al-AFI). Extensive evaluation of the catalytic performance of these AFI zeolites compared with reference conventional zeolite catalysts for alkylation of toluene with isopropyl alcohol showed that deGe-Al-AFI exhibited relatively high toluene conversion and selectivity to valuable p-cymene due to the optimized textural and acidic properties.

Iron-Catalyzed Isopropylation of Electron-Deficient Aryl and Heteroaryl Chlorides

Traditional methods for the preparation of secondary alkyl-substituted aryl and heteroaryl chlorides challenge both selectivity and functional group tolerance. This contribution describes the use of statistical design of experiments to develop an effective procedure for the preparation of isopropyl-substituted (hetero)arenes with minimal isopropyl to n-propyl isomerization. The reaction tolerates electronically diverse aryl chloride coupling partners, with excellent conversion observed for strongly electron-deficient aromatic rings, such as esters and amides. Electron-rich systems, including methyl- and methoxy-substituted aryl chlorides, were found to be less reactive. Furthermore, the reaction was found to be most successful when heteroaryl chlorides were submitted to the cross-coupling protocol. By mapping substituent effects on reaction selectivity, we were able to show that electron-deficient aryl chlorides are essential for efficient coupling, and use electronic structure calculations to predict the likelihood of successful coupling through the estimation of the electron affinity of each aryl chloride. Moderate isolated yields were achieved with selected aryl chlorides, and moderate to good isolated yields were obtained for all the heteroaryl chlorides coupled. Excellent selectivity was observed when a 2,6-dichloroquinoline was used, allowing mono-substitution on a challenging substrate. (Figure presented.).

Heterogeneous Catalytic Hydroarylation of Olefins at a Nanoscopic Aluminum Chlorofluoride

We report on hydroarylation reactions of arenes with olefins under very mild conditions catalyzed heterogeneously by aluminum chlorofluoride (ACF; AlClxF3?x, x≈0.05–0.25). The reactions of benzene and toluene with ethylene or propylene proceed with high conversions to afford various alkylated arenes. For cyclohexene and 1-hexene, the reactions require higher temperatures and the conversions are lower. ACF also catalyzes the hydroarylation of 1,3,5-trifluorobenzene and pentafluorobenzene with ethylene and propylene. The alkylations of arenes with non-fluorinated olefins resemble typical Friedel–Crafts chemistry to give rise to Markovnikov regioselectivity. The reaction of CF3CH=CH2 with benzene proceeds with anti-Markovnikov regioselectivity to give the fluorinated olefin PhCHCH=CF2 and the alkylation product PhCH2CH2CF3 as products of C?F and C?H activation.

Production of p -cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor

Crude sulphate turpentine (CST), containing -pinene, 3-carene, other terpene isomers, and organic sulphur compounds, was used as feedstock in the production of cymenes with commercial zeolite catalysts. The catalysts used were not sensitive to sulphur, and the desulphurisation step was not needed prior to cymene synthesis. The experiments were performed in a continuous fixed bed reactor. Promising results were obtained after initial optimization at temperatures close to 300 °C with faujasite Y zeolite under 5 bar N2 pressure. Cymenes were produced with 54% yields from model compound -pinene and with 28% yields from CST. The mechanistic route of the reaction can be divided into three steps: (1) ring opening, (2) rearrangement, and (3) dehydrogenation. The final step in the formation of p-cymene can occur via dehydrogenation or disproportion; here the effect of reaction conditions and catalyst plays a crucial role.

Polar reactions of acyclic conjugated bisallenes

The chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br2 and I2 addition), and [2 + 2] cycloaddition with chlorosulfonyl isocyanate. The resulting adducts were fully characterized by spectroscopic and analytical methods; they constitute interesting substrates for further organic transformations.

Selective reduction of biomass by hydriodic acid and its in situ regeneration from iodine by metal/hydrogen

HI returns: Hydroiodic acid is a highly selective reducing reagent for a wide variety of substrates. Its application is limited by the formation of iodine and the difficulty in reconverting that iodione back to HI in situ. We report the facile conversion of I2 to HI by metal-catalyzed hydrogenation in the presence of water, and demonstrate the utility of this process in the conversion of fructose to 5-methyfurfural and glycerol to 2-iodopropane. Copyright

Facile fabrication of aluminum-promoted vanadium phosphate: A highly active heterogeneous catalyst for isopropylation of toluene to cymene

Vanadium phosphate is well known as a heterogeneous catalyst in gas phase oxidation reactions. To date, there has been little interest in carrying out liquid-phase reactions with vanadium phosphate as catalyst. Herein, we report the catalytic activity of vanadium phosphate and aluminum-promoted vanadium phosphate toward liquid-phase isopropylation of toluene to cymene. The catalysts were unambiguously characterized by X-ray diffraction, N2 adsorption-desorption, FT-IR technique, UV-vis DRS, and FE-SEM. The total acid sites were estimated by an NH3 TPD analyzer. XPS was used as a powerful tool to know the electronic environment of the catalysts. The optimization of the reaction was carried out by varying temperature from 75 to 150 °C and molar ratio (toluene: isopropanol) from 1:1-1:3. Under optimum reaction conditions, 5 wt.% aluminum-promoted vanadium phosphate showed 90% conversion with 85% selectivity to p-cymene.