94-60-0

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl 1,4-cyclohexanedicarboxylate is used as a reactant for the preparation of cycloalkylamide derivatives, which are inhibitors of the soluble epoxide hydrolase. These inhibitors play a crucial role in the development of drugs targeting various diseases, including hypertension and inflammatory conditions, by modulating the activity of the soluble epoxide hydrolase enzyme.
Used in Chemical Research:
Dimethyl cyclohexane-1,4-dicarboxylate, in the form of a mixture of cis and trans isomers, is utilized in chemical synthesis studies. Researchers use Dimethyl 1,4-cyclohexanedicarboxylate to explore new synthetic pathways, develop novel compounds, and investigate the properties of cyclohexane-based molecules. This contributes to the advancement of organic chemistry and the discovery of new materials and pharmaceuticals.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H16O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h7-8H,3-6H2,1-2H3/t7-,8-

Upstream product

• 67-56-1 methanol 
• 13170-66-6 trans-1,4-cyclohexanedicarboxylic acid chloride 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 619-81-8 cyclohexane-1,4-dicarboxylic acid 
• 22646-79-3 dimethyl 1-cyclohexen-1,4-dicarboxylate 
• 74-88-4 methyl iodide 
• 3588-17-8 trans,trans-muconic acid 
• 19618-93-0 2-cyclohexene-1,4-dicarboxylic acid 
• 6289-46-9 dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate 
• 692-91-1 cis,cis-dimethyl muconate 
• 692-92-2 (2Z,4E)-hexa-2,4-dienedioic acid dimethyl ester 
• 1119-43-3 (E,E)-hexa-2,4-dienedioic acid dimethyl ester 
• 1119-72-8 cis,cis-Muconic acid 
• 1119-73-9 (2Z,4E)-2,4-hexadienedioic acid 

Downstream Products

• 32529-79-6 4-(methoxycarbonyl)cyclohexanecarboxylic acid 
• 22646-79-3 dimethyl 1-cyclohexen-1,4-dicarboxylate 
• 99174-07-9 1-bromo-cyclohexane-1,4-dicarboxylic acid dimethyl ester 
• 120077-75-0 dimethyl 1-acetylcyclohexane-1,4-dicarboxylate 
• 1206201-73-1 dimethyl 1,4-dideuteriocyclohexane-1,4-dicarboxylate 
• 1268629-27-1 methyl 4-(3-phenylpropylcarbamoyl)cyclohexanecarboxylate 
• 1268629-28-2 4-(3-phenylpropylcarbamoyl)cyclohexanecarboxylic acid 
• 1350375-35-7 1-allyl-cyclohexane-1,4-dicarboxylic acid dimethyl ester 
• 1350375-34-6 dimethyl trans-1-(2-oxoethyl)cyclohexane-1,4-dicarboxylate 
• 1855-65-8 1,1,4,4-tetrakis(hydroxymethyl)cyclohexane 
• 105-08-8 bis-1,4-(hydroxymethyl)cyclohexane 
• 33424-83-8 1,4-cyclohexanedicarboxaldehyde 
• 1056639-33-8 4-(methoxycarbonyl)-4-methylcyclohexanecarboxylic acid 
• 34885-03-5 (4-methylcyclohexyl)methanol 

Relevant academic research and scientific papers

Solvent-driven isomerization of: cis, cis -muconic acid for the production of specialty and performance-advantaged cyclic biobased monomers

The quest for green plastics calls for new routes to aromatic monomers using biomass as a feedstock. Suitable feedstock molecules and conversion pathways have already been identified for several commodity aromatics through retrosynthetic analysis. However, this approach suffers from some limitations as it targets a single molecule at a time. A more impactful approach would be to target bioprivileged molecules that are intermediates to an array of commodity and specialty chemicals along with novel compounds. Muconic acid (MA) has recently been identified as a bioprivileged intermediate as it gives access to valuable aliphatic and cyclic diacid monomers including terephthalic acid (TPA), 1,4-cyclohexanedicarboxylic acid (CHDA), and novel monounsaturated 1,4-cyclohexenedicarboxylic acids (CH1DA, CH2DA). However, accessing these cyclic monomers from MA requires to first isomerize biologically-produced cis,cis-MA to Diels-Alder active trans,trans-MA. A major impediment in this isomerization is the irreversible ring closing of MA to produce lactones. Herein, we demonstrate a green solvent-mediated isomerization using dimethyl sulfoxide and water. The mechanistic understanding achieved here elucidates the role of low concentrations of water in reducing the acidity of the system, thereby preventing the formation of lactones and improving the selectivity to trans,trans-MA from less than 5% to over 85%. Finally, a Diels-Alder reaction with trans,trans-MA is demonstrated with ethylene. The monounsaturated cyclic diacid obtained through this reaction (CH1DA) can be converted in a single step into TPA and CHDA, or can be directly copolymerized with adipic acid and hexamethylenediamine to tailor the thermal and mechanical properties of conventional Nylon 6,6.

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.

Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.

POWDERY 1,4-CYCLOHEXANEDICARBOXYLIC ACID

An object of the present invention is to provide a powder of high-purity 1,4-cyclohexanedicarboxylic acid with excellent powder flowability. The invention provides a powder of high-purity 1,4-cyclohexanedicarboxylic acid having particle size distributions (volume basis) such that D10 is within a range of 5 to 55 μm, D50 is within a range of 40 to 200 μm, and D90 is within a range of 170 to 800 μm; and having an aerated bulk density of 0.4 to 0.8 g/cm3, a packed bulk density of 0.5 to 1.0 g/cm3, and a compressibility of 10 to 23%.

Synthesis of gasoline and jet fuel range cycloalkanes and aromatics from poly(ethylene terephthalate) waste

For the first time, gasoline and jet fuel range C7-C8 cycloalkanes and aromatics were selectively synthesized by the alcoholysis of poly(ethylene terephthalate) (PET) waste, followed by solvent-free hydrogenation and hydrodeoxygenation (HDO). It was found that methanol is highly reactive for the alcoholysis of PET waste. In the absence of any catalyst, a high yield of dimethyl terephthalate (97.3%) was achieved under mild conditions (473 K, 3.5 h). Dimethyl terephthalate exists as a solid and can be automatically separated from methanol with a decrease in temperature. Subsequently, dimethyl terephthalate was liquefied to dimethyl cyclohexane-1,4-dicarboxylate by hydrogenation over noble metal catalysts. Among the investigated catalysts, Pt/C exhibited the highest activity. Finally, the dimethyl cyclohexane-1,4-dicarboxylate as obtained was further hydrodeoxygenated to C7-C8 cycloalkanes and aromatics that can be used as gasoline or additives to improve the densities (or volumetric heat value) and sealabilities of current bio-jet fuels. Bimetallic Ru-Cu/SiO2 was found to be a promising HDO catalyst. According to the characterization results, the excellent HDO performance of Ru-Cu/SiO2 can be explained by the formation of smaller Ru-Cu alloy particles during the catalyst preparation. In real applications, dimethyl cyclohexane-1,4-dicarboxylate can also be simultaneously hydrodeoxygenated with biomass derived oxygenates to produce jet fuel with a suitable content of cycloalkanes and aromatics.

Method for preparing dimethyl 1,4-cyclohexanedicarboxylate through ruthenium-rhenium bimetallic catalytic dimethyl terephthalate hydrogenation

The invention provides a method for preparing dimethyl 1,4-cyclohexanedicarboxylate through ruthenium-rhenium bimetallic catalytic dimethyl terephthalate hydrogenation. A supported ruthenium-rhenium bimetallic catalyst is prepared, and is applied to the technical process for preparing dimethyl 1,4-cyclohexanedicarboxylate through dimethyl terephthalate hydrogenation under mild conditions. The reaction is carried out for 1-3 hours under the reaction pressure of 2-5MPa and at the reaction temperature of 30-120 DEG C, the conversion rate of the dimethyl terephthalate can reach 97.91%, and the selectivity on the target product dimethyl 1,4-cyclohexanedicarboxylate can reach 99.88%. The method has the advantages of being mild in reaction conditions, high in catalytic efficiency, simple in catalyst preparation and the like, and has high practicality and economical efficiency.

Preparation method of terephthalic acid and diester thereof

The invention discloses a preparation method of terephthalic acid and diester thereof. Specifically, under the action of a supported metal catalyst, 2-cyclohexene-1,4-dicarboxylic acid undergoes catalytic dehydro-aromatization in a polar solvent or a nonpolar solvent so as to prepare terephthalic acid and diester. The polar solvent is water, methanol, ethanol, n-propanol, isopropanol, n-butanol, glycol dimethyl ether and diglyme. The nonpolar solvent is one or more than two components selected from a group consisting of n-hexane, n-heptane, normal octane, cyclohexane, benzene and toluene. A metal active component of the supported metal catalyst is non-noble metal and/or noble metal. A carrier for the supported metal catalyst is one or more than two components selected from a group consisting of a carbon carrier, nanoscale metal oxide, nanometer nonmetal oxide and a molecular sieve. When conversion rate of 2-cyclohexene-1,4-dicarboxylic acid is 95% and above, selectivity of terephthalic acid or diester of terephthalic acid can reach 90%.

A process for preparing 1,4-cyclohexane dicarboxylic acid diester method

A new method for preparing 1,4-cyclohexane dioctyl phthalate diester. The method comprises: using a succinate diester as a material, obtaining succinyl succinate diester by means of ester condensation, and hydrogenating and dehydrating the succinyl succinate diester to obtain 1,4-cyclohexane dioctyl phthalate diester. The present invention provides a new way for preparing 1,4-cyclohexane dioctyl phthalate diester, and has a very important development potential and a broad application perspective.

METHOD FOR PREPARING DIMETHYL 1,4-CYCLOHEXANEDICARBOXYLATE AND METHOD FOR PREPARING 1,4-CYCLOHEXANEDIMETHANOL

A method for preparing dimethyl 1,4-cyclohexanedicarboxylate (DMCD) is provided. The method includes hydrogenating dimethyl terephthalate (DMT) under a condition of a pressure of 20 to 30 kg/cm2 to continuously prepare the DMCD, and thereby increasing the selectivity of the DMCD. A method for preparing 1,4-cyclohexanedimethanol (CHDM) is further provided.

The role of hydrotalcite-modified porous alumina spheres in bimetallic RuPd catalysts for selective hydrogenation

By utilizing alumina previously modified by in-situ growth of varying amounts of hydrotalcites, a series of heterogeneous bimetallic catalysts with constant low loading (0.3 wt.%) and identical Ru:Pd ratio (1:1) were prepared based on co-impregnation for selective hydrogenation of dimethyl terephthalate to dimethyl cyclohexane-1,4-dicarboxylate. Nanoparticles confined in the reticular structure were observed. The resulting candidates show the superior catalytic activity over that supported on the unmodified alumina, and reach the highest in the optimized sample RuPd/HTC-Al2O 3-1. This promotion and optimization effect could be ascribed to the improved dispersion and more supply of hydrogen and acid sites especially with medium strength.