4331-54-8

Usage

Uses

Used in Chemical Synthesis:
4-Methylcyclohexanecarboxylic acid is used as a key intermediate in the synthesis of various organic compounds, particularly in the production of substituted cyclohexyl carbonyl chlorides. These synthesized compounds find applications in the pharmaceutical, agrochemical, and chemical industries.
Used in Catalytic Hydrogenation:
In the field of catalysis, 4-Methylcyclohexanecarboxylic acid has been utilized to investigate the palladium core-porous silica shell-nanoparticles catalyzed hydrogenation of 4-carboxybenzaldehyde (4-CBA) to p-toluic acid. This application highlights its role in the development of efficient and selective catalytic processes for the production of valuable chemicals and pharmaceutical intermediates.
Used in Pharmaceutical Industry:

InChI:InChI=1/C8H14O2/c1-6-2-4-7(5-3-6)8(9)10/h6-7H,2-5H2,1H3,(H,9,10)

Upstream product

• 1879-06-7 4-acetyl-1-methylcyclohexane 
• 524048-18-8 4-methylcyclohexane-1-carbonitrile 
• 99-94-5 p-Toluic acid 
• 15719-64-9 methylammonium carbonate 
• 591-49-1 1-methylcyclohex-1-ene 
• 201230-82-2 carbon monoxide 
• 33242-79-4 4-methylcyclohexanecarbaldehyde 
• 64-19-7 acetic acid 
• 123-51-3 i-Amyl alcohol 
• 99-82-1 Menthane 
• 638-38-0 manganese(II) acetate 
• 301-04-2 lead acetate 
• 5333-31-3 4-methylcyclohex-1-ene-1-carboxylic acid 
• 2207-04-7 trans-1,4-dimethylcyclohexane 

Downstream Products

• 41692-50-6 trans-4-methyl-1-(ethoxycarbonyl)cyclohexane 
• 60940-94-5 cis-4-methyl-cyclohexane-carboxylic acid-⁽¹⁾-amide 
• 7133-31-5 4-methylcyclohexanecarboxylic acid ethyl ester 
• 104907-47-3 2-chloro-3-(trans-4-methylcyclohexyl)-1,4-naphthoquinone 
• 104907-48-4 2-chloro-3-(cis-4-methylcyclohexyl)-1,4-naphthoquinone 
• 34885-03-5 (4-methylcyclohexyl)methanol 
• 848170-53-6 cis/trans-N-methoxy-N,4-dimethylcyclohexanecarboxamide 
• 910910-20-2 (1r,4r)-N-methoxy-N,4-dimethylcyclohexane-1-carboxamide 
• 910910-21-3 4-methyl-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 33242-79-4 4-methylcyclohexanecarbaldehyde 

Relevant academic research and scientific papers

Electrocatalytic hydrogenation of benzoic acids in a proton-exchange membrane reactor

The highly efficient chemoselective electrocatalytic hydrogenation of benzoic acids (BAs) to cyclohexanecarboxylic acids (CCAs) was carried out in a proton-exchange membrane reactor under mild conditions without hydrogenation of the carboxyl group. Among the investigated catalysts, the PtRu alloy catalyst was found to be the most suitable for achieving high current efficiencies for production of CCAs. An electrochemical spillover mechanism on the PtRu alloy catalyst was also proposed.

Towards the Circular Economy: Converting Aromatic Plastic Waste Back to Arenes over a Ru/Nb2O5 Catalyst

The upgrading of plastic waste is one of the grand challenges for the 21st century owing to its disruptive impact on the environment. Here, we show the first example of the upgrading of various aromatic plastic wastes with C?O and/or C?C linkages to arenes (75–85 % yield) via catalytic hydrogenolysis over a Ru/Nb2O5 catalyst. This catalyst not only allows the selective conversion of single-component aromatic plastic, and more importantly, enables the simultaneous conversion of a mixture of aromatic plastic to arenes. The excellent performance is attributed to unique features including: (1) the small sized Ru clusters on Nb2O5, which prevent the adsorption of aromatic ring and its hydrogenation; (2) the strong oxygen affinity of NbOx species for C?O bond activation and Br?nsted acid sites for C?C bond activation. This study offers a catalytic path to integrate aromatic plastic waste back into the supply chain of plastic production under the context of circular economy.

Catalytic hydrogenation products of aromatic and aliphatic dicarboxylic acids

Hydrogenation of aromatic dicarboxylic acids gave 100 % selectivity to respective cyclohexane dicarboxylic acid with 5 % Pd/C catalyst. 5 % Ru/C catalyst was observed to give over hydrogenation products at 493 K and at lower temperature (453 K) the selectivity for cyclohexane dicarboxylic acids was increased. Hydrogenation of phthalic acid with Ru-Sn/Al2O3 catalyst was observed to give phthalide instead of 1,2-benzene dimethanol or 2-hydroxy methyl benzoic acid. Ru-Sn/Al2O3 catalyst selectively hydrogenated the carboxylic group of cyclohexane dicarboxylic acids to give cyclohexane dimethanol. Use of proper catalysts and reaction conditions resulted in desired products.

Selective hydrogenation of benzoic acid to cyclohexane carboxylic acid over microwave-activated Ni/carbon catalysts

High yields of cyclohexane carboxylic acids were obtained by direct hydrogenation of aromatic carboxylic acids over different Ni/carbon catalysts having distinctive surface properties. The catalysts were characterized by SEM, TEM, H2-TPR and N2 adsorption isotherms for the determination of BET surface area and porosity. The hydrogenation reaction was carried out in batch pressure reactor in gas-liquid phase at 200 °C. High selectivity (100%) of cyclohexane carboxylic acids at 86.2 mol% conversion of benzoic acid was achieved over microwave-activated biochar supported non-precious metal Ni catalyst. The 10%Ni/CSC-b catalyst has been investigated for hydrogenation of benzoic acid to cyclohexane carboxylic acids and shown little deactivation in stability test. The effects of Ni loading, high dispersion of Ni species, appropriate power of microwave heating and strong interaction of Ni species with carbon are of benefit to the reaction.

Selective hydrogenation of aromatic carboxylic acids over basic N-doped mesoporous carbon supported palladium catalysts

Mesoporous carbon nitride (MCN) has been prepared through a simple polymerization reaction between ethylenediamine (EDA) and carbon tetrachloride (CTC) by a nano hard-templating approach. The obtained MCN possesses high surface area (166.3 m2/g), average pore size of 9.2 nm and high N content (up to 18.5 wt%). The negative charge and the basicity on MCN surface are originated from its rich carbon nitride heterocycles, which notably improves the surface hydrophilicity and the adsorption of acidic molecules. Furthermore, MCN can be adopted as the proper support for highly dispersed Pd NPs with well-controlled size distribution. Compared with microporous N-doped active carbon with low N-content, the MCN-supported Pd catalyst shows an enhanced activity in water phase for the selective ring hydrogenation of benzoic acid, benzamide and phenol, in which 11.3 times higher activity in comparison to undoped catalyst is achieved. Wide characterizations reveal that big pore size, selective adsorption for acid substrate and strong interaction between N and Pd may lead to the high activity of Pd/MCN.

NOVEL COMPOUNDS

Novel rapamycin analogues and methods for their production with FKBP and/or MIP inhibitory activity with reduced mTOR inhibitory activity with therapeutic potential e.g. as bacterial virulence inhibitors.

Carbon dioxide as a C1 building block for the formation of carboxylic acids by formal catalytic hydrocarboxylation

A happy marriage of two processes: An effective catalytic system was identified for the direct synthesis of carboxylic acids from non-activated olefins or alcohols, CO2, and H2. Detailed analysis together with labeling studies indicated that the overall hydrocarboxylation of simple olefins results from a combination of the reverse water-gas shift (rWGS) reaction and a hydroxycarbonylation step, each promoted by a rhodium catalyst (see scheme). Copyright

Experimental determination of the conformational free energies (A values) of fluorinated substituents in cyclohexane by dynamic 19F NMR spectroscopy. Part 2. Extension to fluoromethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthio and trifluoromethoxy groups

The synthesis of monosubstituted and 1,4-substituted cyclohexanes bearing one of the title groups is described. The conformational analysis of these compounds was studied by 19F NMR spectroscopy at various temperatures. Chemical shifts for each conformer above the coalescence temperature were obtained by binomial regression from low temperature values, allowing the high precision determination of the equilibrium constants, and the corresponding thermodynamic parameters (ΔG°, ΔH°, ΔS°) of the fluorinated substituents. For A values (-ΔG°298K), the following averaged data were obtained: 1.59 (CFH2), 1.85 (CF2H), 2.67 (C2F5), 0.79 (OCF3) and 1.18 (SCF3) [in kcal mol-1]. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

Improved synthesis of trans-4-alkylcyclohexane carboxylic acids

Several stereomerically pure amino acid derivatives containing the N-terminal trans-4-alkylcyclohexanoyl fragment were obtained. Hydrogenation of 4-alkylbenzoic acids in the presence of a special Ru-Ni/C catalytic system and isomerization of the resulting mixture of trans- and cis-isomers of 4-alkylcyclohexanecarboxylic acids were used as the key steps. The stereomeric configuration of all compounds was confirmed by 1H NMR spectroscopy. The compounds obtained possess a broad biological activity potential and are useful intermediates in the synthesis of stereomerically pure modified peptides.

METHOD FOR PRODUCING TRANS-1,4-CYCLOHEXANE DICARBOXYLIC ACID

A subject for the invention is to obtain trans-1,4-cyclohexanedicarboxylic acid (t-CHDA) in a high concentration by efficiently isomerizing cis-1,4-cyclohexanedicarboxylic acid (c-CHDA) by a simple method. The invention provides: (1) a process for producing t-CHDA which comprises heating crude CHDA to 180°C or higher in an inert atmosphere and causing the t-CHDA formed by isomerization to precipitate in the molten c-CHDA while holding the crude CHDA at a temperature in the range of not lower than 180°C and less than the melting point of t-CHDA; (2) a process for producing t-CHDA, wherein crude CHDA which is powdery or granular is heat-treated at a temperature of not lower than the melting point of c-CHDA and lower than the melting point of t-CHDA to thereby isomerize the cis isomer to the trans isomer while maintaining the powdery or granular state; (3) a process for producing t-CHDA, wherein crude CHDA is held at a temperature of not lower than the melting point of c-CHDA and lower than the melting point of t-CHDA in an inert atmosphere while maintaining flowing to thereby obtain powdery or granular t-CHDA; and (4) a process for purifying crude CHDA in which crude CHDA obtained through the step of hydrogenating TPA or the like is heated in an atmosphere of an inert gas to volatilize and remove impurities.