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98-89-5

98-89-5

Identification

  • Product Name:Cyclohexanecarboxylic acid

  • CAS Number: 98-89-5

  • EINECS:202-711-3

  • Molecular Weight:128.171

  • Molecular Formula: C7H12O2

  • HS Code:29172090

  • Mol File:98-89-5.mol

Synonyms:FEMA No. 3531;4-09-00-00016 (Beilstein Handbook Reference);7549-42-0;Cyclohexylmethanoic acid;Cyclohexanoic acid;50825-29-1;Cyclohexylformic acid;EPA Pesticide Chemical Code 112603;Cyclohexanecarboxylic acid, calcium salt;Hexahydrobenzoic acid;Cyclohexane Carboxylic Acid;cyclohexanecarboxylic acid;hexahydrobenzoic acid;Cyclohexanecarboxylicacid;Sodium Hexametaphosphate;hexahydro-;136-01-6;Benzoic acid, hexahydro-;Cyclohexane-1-carboxylate;Hexahyl carbonic acid;Cyclohexanecarboxylic acid, sodium salt;25666-60-8;

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  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

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Relevant articles and documentsAll total 319 Articles be found

Stahl,Balaceanu

, p. 684 (1958)

Palladium and copper-catalyzed carboxylation of alkanes with carbon monoxide. Remarkable effect of the mixed metal salts

Nakata,Miyata,Jintoku,Kitani,Taniguchi,Takaki,Fujiwara

, p. 3755 - 3759 (1993)

The mixed catalyst Pd(OAc)2-Cu(OAc)2 promotes the carboxylation of cyclohexane and propane with CO in higher yield than either a Pd(II) or Cu(II) catalyst alone. The mixed catalyst has the highest activity when the ratio of Cu(II)/Pd(II) is more than unity. The carboxylations of p-xylene with Pd(II)-Cu(II) and Pd(II) afford 2,5-dimethylbenzoic acid, but no carboxylic acid is detected in the reaction with Cu(II), giving rise to p- xylene dimer as the major product instead. Clear isotope effect (3.0-3.2) is observed in the reactions of cyclohexane with Pd(II)-Cu(II) and Pd(II), unlike the reaction with Cu(II) (1.0).

Ring hydrogenation of aromatic compounds in aqueous suspensions of an Rh-loaded TiO2 photocatalyst without use of H2 gas

Nakanishi, Kousuke,Yagi, Ryosuke,Imamura, Kazuya,Tanaka, Atsuhiro,Hashimoto, Keiji,Kominami, Hiroshi

, p. 139 - 146 (2018)

There are various possibilities of co-catalyst-assisted photocatalytic reduction (CPR) over a titanium(iv) oxide (TiO2) photocatalyst, especially H2-free and chemoselective CPR. We examined the photoinduced ring hydrogenation of aromatics having a carboxyl group over metal-loaded TiO2 under H2-free conditions and found that the aromatics were almost quantitatively hydrogenated to the corresponding cyclohexanes having a carboxyl group when rhodium, water and oxalic acid were used as a metal co-catalyst, solvent and hole scavenger, respectively. The effects of different metal co-catalysts, solvents and hole scavengers on the ring hydrogenation were also examined. Based on the results obtained under various conditions, the light dependency and adsorption behavior of the aromatics and hole scavengers, the functions of TiO2 and the co-catalyst, and the reaction process are discussed.

Palladium Catalyzed Carboxylation of Cyclohexane with Carbon Monoxide

Nakata, Kazuyuki,Watanabe, Jun,Takaki, Ken,Fujiwara, Yuzo

, p. 1437 - 1438 (1991)

Very high turnover numbers of the catalyst in direct carboxylation of cyclohexane with CO have been obtained using palladium catalyst, to give 8.8percent yield (turnover number 205) of cyclohexanecarboxylic acid based on the starting alkane.

Boosting Catalysis of Pd Nanoparticles in MOFs by Pore Wall Engineering: The Roles of Electron Transfer and Adsorption Energy

Chen, Dongxiao,Yang, Weijie,Jiao, Long,Li, Luyan,Yu, Shu-Hong,Jiang, Hai-Long

, (2020)

The chemical environment of metal nanoparticles (NPs) possesses significant influence on their catalytic performance yet is far from being well understood. Herein, tiny Pd NPs are encapsulated into the pore space of metal–organic frameworks (MOFs), UiO-66-X (X = H, OMe, NH2, 2OH, 2OH(Hf)), affording Pd@UiO-66-X composites. The surface microenvironment of the Pd NPs is readily modulated by pore wall engineering, via the functional group and metal substitution in the MOFs. Consequently, the catalytic activity of Pd@UiO-66-X follows the order of Pd@UiO-66-OH > Pd@UiO-66-2OH(Hf) > Pd@UiO-66-NH2 > Pd@UiO-66-OMe > Pd@UiO-66-H toward the hydrogenation of benzoic acid. It is found that the activity difference is not only ascribed to the distinct charge transfer between Pd and the MOF, but is also explained by the discriminated substrate adsorption energy of Pd@UiO-66-X (–OH 2 –OMe –H), based on CO-diffuse reflectance infrared Fourier transform spectra and density-functional theory (DFT) calculations. The Pd@UiO-66-OH, featuring a high Pd electronic state and moderate adsorption energy, displays the highest activity. This work highlights the influence of the surface microenvironment of guest metal NPs, the catalytic activity of which is dominated by electron transfer and the adsorption energy, via the systematic substitution of metal and functional groups in host MOFs.

In-situ generated highly dispersed nickel nanoclusters confined in MgAl mixed metal oxide platelets for benzoic acid hydrogenation

Zhang, Huiling,Dong, Jie,Qiao, Xianliang,Qin, Jingru,Sun, Haofei,Wang, Aiqing,Niu, Libo,Bai, Guoyi

, p. 258 - 265 (2019)

A new and cost-effective NiMgAl mixed metal oxide (Ni2Mg0.5Al1-MMO) catalyst derived from hierarchical flower-like Ni-Mg-Al layered double hydroxides (NiMgAl-LDHs) was fabricated by a hydrothermal-calcination-reduction method. This catalyst showed excellent catalytic performance in the selective hydrogenation of benzoic acid to cyclohexanecarboxylic acid. Notably, recycling experiments demonstrated that this catalyst could be used at least ten times without significant losses in activity and selectivity under harsh reaction conditions; thus, it presents similar behavior to most of noble metal catalysts. A series of characterizations were performed to investigate the relationship between the structure and the catalytic performance of this catalyst and elucidate the mechanism of its good stability. The results demonstrated that the Ni2Mg0.5Al1-MMO catalyst exhibited highly dispersed nickel species due to the well-defined flower-like structure of NiMgAl-MMO platelets as well as the confined effect of Mg and Al oxide species.

Highly effective Ir-based catalysts for benzoic acid hydrogenation: Experiment- and theory-guided catalyst rational design

Tang, Minghui,Mao, Shanjun,Li, Xuefeng,Chen, Chunhong,Li, Mingming,Wang, Yong

, p. 1766 - 1774 (2017)

On the way to exploring superior hydrogenation catalysts, Ir-based catalysts with a record catalytic activity (up to 40 h-1) for the hydrogenation of benzoic acid to cyclohexanecarboxylic acid under mild reaction conditions (85 °C, 0.1 MPa H2, in water) have been successfully developed. By excluding various factors, the experimental results showed that the main factor governing the activity discrepancy between the Ir-based catalysts is actually the dispersion stability of the supports (such as N-doped carbon, active carbon, SBA-15 and various metal oxides) in the reaction solution, rather than the interaction between the Ir active component and the supports. Combined with theoretical investigation from first principles, an activity volcano curve considering the competing adsorption between the reactants (H2) and solvent (H2O) for aqueous aromatic ring hydrogenation was presented for the first time. The high activity of Ir can be deduced by the proper discrepancy of dissociation energies or adsorption energies between H2 and H2O on the catalysts. This activity volcano curve provides guidance for further rational design of promising catalysts for benzoic acid or even aromatic ring hydrogenation under true reaction conditions for practical applications.

RuPd alloy nanoparticles supported on N-doped carbon as an efficient and stable catalyst for benzoic acid hydrogenation

Tang, Minghui,Mao, Shanjun,Li, Mingming,Wei, Zhongzhe,Xu, Fan,Li, Haoran,Wang, Yong

, p. 3100 - 3107 (2015)

RuPd alloy nanoparticles (3.6 nm) uniformly dispersed on N-doped carbon (RuPd/CN) was prepared via a simple ultrasound-assisted coreduction method. The RuPd/CN is highly active, selective, and stable in the hydrogenation of benzoic acid to cyclohexanecarboxylic acid under mild conditions with a TOF up to 2066 h-1. It was found that the bimetallic RuPd/CN catalyst exhibited a substantially enhanced activity in comparison with the monometallic catalysts (Ru/CN and Pd/CN). The reason for the higher performance of the RuPd/CN catalyst is considered to be the increased Ru0 /Run+ ratio induced by the electronic interaction between Ru and Pd, as evidenced by various characterizations. Notably, the different phenomenon of activity platform on different catalysts ascribed to the effect of hydrogen pressure was newly observed and further explained by first-principle studies. Moreover, the factors influencing the adsorption modes of BA, especially the configuration of the carboxyl group, have been investigated preliminarily in first-principle studies, giving a distinct insight from the former work. The reason the carboxyl group in benzoic acid does not undergo hydrogenation, which results in superior selectivity (>99%), is also revealed by a comparison of the thermodynamics of hydrogenation and dissociation of the carboxyl group.

A highly dispersed and stable Ni/mSiO2-AE nanocatalyst for benzoic acid hydrogenation

Zhang, Huiling,Gao, Xuejia,Ma, Yuanyuan,Han, Xue,Niu, Libo,Bai, Guoyi

, p. 5993 - 5999 (2017)

A Ni/mSiO2-AE nanocatalyst was successfully prepared via loading the active nickel species on mSiO2 by an ammonia evaporation (AE) method. It exhibited excellent catalytic performance in the selective hydrogenation of benzoic acid with the conversion of benzoic acid and selectivity to cyclohexane carboxylic acid being 98.9% and 99.1%, respectively. Furthermore, the catalyst can be recycled four times without appreciable loss of its initial activity. As demonstrated by TEM, the active nickel species was highly dispersed with an average particle size of 3.2 nm in this nanocatalyst, which is much smaller than that of Ni/mSiO2-IMP (~18 nm), prepared by a conventional impregnation method. TPR and XPS results revealed the existence of a stronger interaction between the active nickel species and the mSiO2 support in Ni/mSiO2-AE, compared to Ni/mSiO2-IMP. This strong metal-support interaction in Ni/mSiO2-AE can effectively suppress the loss of the active nickel species during the reaction, resulting in its good stability under relatively harsh reaction conditions.

Multifunctional solid surfaces for enhanced catalysis

Motokura, Ken

, p. 3067 - 3068 (2014)

-

Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading

Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui

, (2021/12/13)

Acceptorless dehydrogenative coupling (ADC) of alcohols and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, we designed and fabricated a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1], the superior complex in our previous work. Gratifyingly, gram-scale synthesis of carboxylic acids was efficiently enabled at an ultralow Ru loading (62.5 ppm) in open air. Moreover, effects of distinct ancillary NHC ligands and other parameters on this catalytic process were thoroughly studied, while further systematic studies were carried out to provide rationales for the activity trend of [Ru-1]-[Ru-7]. Finally, determination of quantitative green metrics illustrated that the present work exhibited superiority over representative literature reports. Hopefully, this study could provide valuable input for researchers who are engaging in metal-catalyzed ADC reactions.

Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**

Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten

supporting information, (2022/01/22)

A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.

Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis

Cao, Haoying,Ma, Shanshan,Feng, Yanhong,Guo, Yawen,Jiao, Peng

supporting information, p. 1780 - 1783 (2022/02/17)

Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun

supporting information, p. 2020 - 2024 (2022/03/31)

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach

Skrotzki, Eric A.,Vandavasi, Jaya Kishore,Newman, Stephen G.

, p. 14169 - 14176 (2021/06/30)

Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to overoxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time to achieve improved control and chemoselectivity over this challenging transformation. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C-H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.

Process route upstream and downstream products

Process route

isophthalic acid
121-91-5

isophthalic acid

cyclohexane-1,3-dicarboxylic acid
3971-31-1

cyclohexane-1,3-dicarboxylic acid

3-methylcyclohexanecarboxylic acid
13293-59-9

3-methylcyclohexanecarboxylic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With 5% active carbon-supported ruthenium; hydrogen; In 1,4-dioxane; at 219.84 ℃; for 12h; under 51680.2 Torr;
cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With water; hydrogen; at 59.84 ℃; for 4h; under 60006 Torr; Reagent/catalyst; Temperature; Pressure; Autoclave; Sealed tube;
carbon monoxide
201230-82-2

carbon monoxide

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With RhCl(CO)(PMe3)2; for 26.5h; under 760 Torr; Yield given. Yields of byproduct given; Ambient temperature; Irradiation;
benzoic acid
65-85-0,8013-63-6

benzoic acid

cyclohexene-1-carboxylic acid
636-82-8

cyclohexene-1-carboxylic acid

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With hydrogen; In benzene; at 100 ℃; for 1h; under 15001.5 Torr; Reagent/catalyst; Solvent; Catalytic behavior;
benzoic acid
65-85-0,8013-63-6

benzoic acid

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With hydrogen; In hexane; at 149.84 ℃; for 5h; under 37503.8 Torr; chemoselective reaction; Autoclave;
With platinum on activated charcoal; hydrogen; In 1,4-dioxane; at 190 ℃; under 22502.3 Torr;
cinnamyl cyclohexanecarboxylate

cinnamyl cyclohexanecarboxylate

1-propenylbenzene
873-66-5

1-propenylbenzene

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
In acetonitrile; Electrochemical reaction;
ethanol
64-17-5

ethanol

benzaldehyde
100-52-7

benzaldehyde

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
cyclohexenone
930-68-7

cyclohexenone

O-cyclohexylcarbonyl benzaldoxime

O-cyclohexylcarbonyl benzaldoxime

3-cyclohexylcyclohexanone
7122-93-2

3-cyclohexylcyclohexanone

benzaldehyde
100-52-7

benzaldehyde

benzonitrile
100-47-0

benzonitrile

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With di-tert-butyl peroxide; In cyclohexane; for 6h; Product distribution; Irradiation;
cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

3-chlorobenzoate
535-80-8

3-chlorobenzoate

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With Boc-L-(?-Me)-His-AGly-L-Cha-L-Phe-NH-TEMPO; 3-chloro-benzenecarboperoxoic acid; In toluene; at 20 ℃; for 15h;
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2478-38-8

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

para-coumaric acid
7400-08-0,50940-26-6

para-coumaric acid

3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
Conditions Yield
With triethylamine methanesulfonic acid; at 70 ℃; for 3h; Overall yield = 10.1 %; Electrochemical reaction; Inert atmosphere;

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