626-70-0

Usage

InChI:InChI=1/C7H12O4/c1-5(7(10)11)3-2-4-6(8)9/h5H,2-4H2,1H3,(H,8,9)(H,10,11)/p-2/t5-/m0/s1

Upstream product

• 591-24-2 3-Methylcyclohexanone 
• 583-59-5 2-Methylcyclohexanol 
• 591-23-1 m-methylcyclohexanol 
• 1670-46-8 2-acetylcyclopentanaone 
• 590-67-0 1-Methylcyclohexanol 
• 1208-47-5 (E)-2-benzylidene-6-methylcyclohexanone 
• 67-64-1 acetone 

Downstream Products

• 110-15-6 succinic acid 
• 20470-38-6 2-[(2,4-Dinitro-phenyl)-hydrazono]-5-methyl-hexanedioic acid dimethyl ester 
• 119639-69-9 1-((E)-(2-methylcyclopentylidiene)methyl)benzene 
• 7470-84-0 2-methyl-adipic acid dianilide 

Relevant academic research and scientific papers

Reactions of hydrogen peroxide with acetylacetone and 2- acetylcyclopentanone

A reaction of acetylacetone with equimolar amount of concentrated aqueous H2O2 in both organic solvents (ButOH, AcOH) and water at various temperatures gave the corresponding 3,5-dihydroxy-1,2- dioxolanes with different configuration of stereogenic centers. In the pres-ence of an excess of H2O2, 3,5-dihydroxy-1,2-dioxolanes were converted to a mixture of 5-hydroperoxy-3-hydroxy-1,2-dioxolanes and further to a mixture of dimeric 1,2-dioxolan-3-ylperoxides. All the peroxides formed exist in solutions as equilibrium mixtures with the starting reagents. A prolonged reflux of solutions of 3,5-dihydroxy-1,2-dioxolanes in ButOH in the presence of a large excess of H2O2 led to the skeletal rearrangements of the substrates to a mixture of propionic acid and hydroxyacetone, which underwent further oxidative transfor-mations. Unlike acetylacetone, 2-acetylcyclopentanone reacted with H2O2 in aqueous phase or in solutions in ButOH under thermodynamic or kinetic control with the formation of the corresponding 5-hydroperoxy-3-hydroxy- 1,2-dioxolanes, rather than 3,5-dihydroxy-1,2-di-oxolanes. Thermodynamically controlled process in solution in AcOH gave a mixture of all four possible hydroperoxyhydroxy-1,2-dioxolanes. These cyclic peroxides in solutions in ButOH or AcOH readily converted to a mixture of AcOH, glutaric, α-methyladipic, and α-hydroxy-α-methyladipic acids. An active α-hydroxylation of the substrate was observed upon reflux of a solution of 2-acetylcyclopentanone and H2O2 in AcOH.

PROCESS FOR PRODUCING ALIPHATIC DICARBOXYLIC ACID COMPOUND

The present invention discloses a process for producing an aliphatic dicarboxylic acid compound, which comprises oxidizing, with a nitrite or a nitrate in the presence of trifluoroacetic acid, an alicyclic secondary alcohol compound or an alicyclic ketone compound, in each of which at least one methylene group is bonded to the carbon atom having hydroxyl group bonded thereto or the carbon atom as a member of carbonyl group, wherein the reaction is conducted in the presence of water of 5 mass % or less relative to 100 mass % of the total of the trifluoroacetic acid and the water.

Efficient oxidation of cycloalkanols by sodium nitrite with molecular oxygen in trifluoroacetic acid

Oxidation of aliphatic cycloalkanols by sodium nitrite in trifluoroacetic acid gave α,ω-dicarboxylic acids in good yields. Adipic acid was obtained in a quantitative yield from cyclohexanol using 1 equiv of sodium nitrite under oxygen atmosphere but the oxidation required more than 3 equiv of sodium nitrite under nitrogen atmosphere. The oxidation method was applicable to the conversion of 1-alkanols to the corresponding carboxylic acids.

Ozonolysis of 1-methylcyclohexanol

The kinetic features and composition of products of 1-methylcyclohexanol ozonolysis were studied.