Catalytic Oxidation of Alcohol to Carboxylic Acid with a Hydrophobic Cobalt Catalyst in Hydrocarbon Solvent

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1 DOI: /asia Full Paper Alcohol Oxidation Catalytic Oxidation of Alcohol to Carboxylic Acid with a Hydrophobic Cobalt Catalyst in Hydrocarbon Solvent Song Shi, [a] Meng Liu, [a, b] Li Zhao, [a, b] Min Wang, [a] Chen Chen,* [a] Jin Gao, [a] and Jie Xu* [a] Abstract: A hydrophobic cobalt catalyst was synthesized and proved to be effective in alcohol oxidation under the assistance of hydrocarbon solvent with oxygen as the terminal oxidant. A series of catalysts with different water contact angles was applied to investigate the hydrophobic effect. Further insight into the reaction process was gained by reaction kinetics, isotopic effect, etc. It showed that the hydrocarbon solvent participated in the alcohol oxidation, and with the aid of the in situ generated free radicals, the a-c H bond was smoothly activated and the alcohol was converted to carbonyl compounds. The hydrophobic effect promoted the alcohol oxidation by affecting the solvent oxidation. Introduction Selective oxidation of alcohols into carbonyl compounds is of great importance at both the laboratory and industrial levels. [1] In recent years, the oxidation of primary alcohols has been frequently reported. [2] Several groups have tried different catalysts and reactors for the selective oxidation of alcohols to aldehydes. [3] Deep-oxidation products of primary alcohols especially for non-activated aliphatic alcohols to carboxylic acids or esters is also an important issue, which show wide applications in detergents, paints, and cosmetics, etc. [4] So far, most of the reported catalysts for the synthesis of carboxylic acid from alcohol under mild conditions are based on noble metals such as palladium, gold, and platinum, and bases are generally needed. [5] Recently, through modifying the support, we have achieved the oxidation of primary aliphatic alcohols to acids in the absence of base. [6] However, the noble metal platinum was still necessary. The limited availability and high price of noble metals constrict their application in large-scale industrial production. Catalysts that contain earth-abundant element such as Co, [7] Fe, [8] Mn, [9] and Cu [10] are attractive both from environmental and economic considerations. However, when these non-noble metals were used as heterogeneous catalysts, the [a] Dr. S. Shi, M. Liu, L. Zhao, Dr. M. Wang, Prof. C. Chen, Prof. J. Gao, Prof. J. Xu State Key Laboratory of Catalysis Dalian Institute of Chemical Physics Chinese Academy of Sciences Dalian National Laboratory for Clean Energy Dalian (China) chenchen@dicp.ac.cn xujie@dicp.ac.cn [b] M. Liu, L. Zhao University of Chinese Academy of Sciences Beijing (China) Supporting information for this article can be found under: efficiencies are generally lower than the noble catalysts no matter of the activity or substrate scope. [11] In addition, a large excess of base additives or explosive oxidizing agents (e.g., peroxy acids or metal oxidants) are generally required to promote the activity and selectivity. [12] Examples reported by Matthias Beller s group showed that the pyrolysis of nitrogen-ligated cobalt(ii) acetate supported on commercial carbon could convert alcohol to ester in excellent yield. [13] In this process, however, extra base is necessary. In terms of economy and environmental friendliness, it is highly desirable to employ a catalyst with earth-abundant elements under base-free conditions by using molecular oxygen (ideally air) as the terminal oxidant. The hydrophobic effect has been proved to be effective in many catalytic fields. The catalytic activity, product selectivity, and catalyst stability are strongly related to the catalyst hydrophobicity. [14] For example, hydrophobic modification of the catalyst could enhance the selectivity for 5-hydroxymethylfurfural in the fructose dehydration process. [15] Our group proved the hydrophobic effect could enhance the activity of the catalyst towards hydrocarbon oxidation. [16] Nevertheless, to gain more insight into the hydrophobic effect in the catalyst field is still important work. In addition, the solvent in the present work was another important factor. The solvent effect is one of the fundamental phenomena in general chemistry, kinetics, and catalysis. The solvent may play a passive or an active role, as it may be involved in the elementary reaction steps. In the present work, the hydrocarbon solvent was proved to participate in the reaction, and with the aid of the in situ generated free radicals, the a-c H bond was smoothly activated and the alcohol was converted to carbonyl compounds. Herein, we first report a hydrophobic cobalt catalyst for alcohol oxidation under the assistance of hydrocarbon solvent. The hydrophobic effect was proved to be effective in the catalytic process. This process provides a new route for alcohol oxidation. Chem. Asian J. 2017, 00, 0 0 These are not the final page numbers! ÞÞ Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim &&

2 Results and Discussion Table 1. Aerobic oxidation of different alcohols. Catalytic results with hydrophobic catalyst Utilizing a reverse-phase micro-emulsion method, hydrophobic silica-based cobalt-containing nanoparticles (Co-Pr-15) were prepared with cobalt ions distributed in the matrix of silica and propyl groups on the surface. The catalyst shows the morphology of spheres with fluffy surfaces (Figures S1 and S2 in the Supporting Information). With organic silane introduced during hydrolysis, the catalyst had organic groups on the surface demonstrated by the asymmetric and symmetric stretching vibration absorptions of the saturated C H bond, which emerged at around 2930 cm 1 in the FTIR spectrum (Figure S3 in the Supporting Information) and showed hydrophobic character with water contact angles (WCA) of The cobalt content determined by inductively coupled plasma (ICP) is only 2.27 %. The three absorption peaks (525, 583, and 645 nm) in the UV/Vis spectra were unambiguously assigned to Co(II) in a tetrahedral environment. Another broad absorption was centered at 356 nm, assigned to a Co(III) species (Figure S4 in the Supporting Information). p-methylbenzyl alcohol was selected as the model molecule to test the catalyst. During the catalytic application, with ethylbenzene as the solvent, p-methylbenzyl alcohol was nearly completely converted to p-methylbenzoic acid (Table 1, entry 1). As a comparison, with commercial and Co 2 O 3, the alcohol hydrophilic catalysts Co 3 O 4 conversion is only about 60% conversion (Table S1 in the Supporting Information). These control experiments clearly showed the hydrophobic catalyst gained the advantage in this catalytic process. Correlating ln(c t /C 0 )(C stands for concentration) against reaction time (s) indicated a linear relationship and a first-order reaction with respect to p-methylbenzyl alcohol (Figure S5 in the Supporting Information). The apparent activation energy, E a, determined from the Arrhenius plot (Figures S6 and S7 in the Supporting Information), is 69.2 kj mol 1. To show the hydrophobic effect, a series of catalysts with different amounts of functionalized organic groups were used as the catalysts. The C H bond peak appeared in the FTIR spectra and its intensity increased with the increase in the ratio of n-propyltrimethoxysilane (PTMS)/tetraethylorthosilicate (TEOS) (Figure S3 in the Supporting Information). The hydrophobicity increased with the increase in propyl group content, as evident from the WCA. As expected, a positive correlation was observed with the increase of WCA (Figure 1); the reaction rate of alcohols increased. This further confirmed the surface hydrophobicity is favorable for oxidation, which will be further discussed below. Various substrates were tested in the oxidation. As seen in Table 1, aromatic primary alcohols were converted to acids with 96 99% conversion and 89 99% selectivity. Aliphatic primary alcohols were also converted with moderate conversion Entry Reactants Products Conv. [%] 1 > Select. [%] 2 > 99 > 99 3 > > 99 > 99 5 > 99 > 99 6 > [a] [b] trace 9 [b] trace Reaction conditions: 10 ml solvent, 1 mmol substrate, 1208C, 4 h, catalyst: 50 mg Co-Pr-15, 1.0 MPa O 2. [a] 3 mmol substrate. [b] Butylated hydroxytoluene (BHT) added. (54 72 %) and high selectivity to acid (80 85%). Secondary alcohols were converted to the corresponding ketones (Table 1, Figure 1. Reaction rates of p-methylbenzyl alcohol with different hydrophobic catalysts. Reaction conditions: 10 ml solvent, 1 mmol substrate, 1208C, 50 mg catalyst, 1.0 MPa O 2. && Chem. Asian J. 2017, 00, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ÝÝ These are not the final page numbers!

3 entries 5, 10). These results illustrated that the reported method is effective for the oxidation of a wide range of alcohols. The effect of the C H BDE of alcohols Various alcohols with different a-c H bond dissociative energies (BDEs) were also studied with ethylbenzene as the solvent (Figure 2 (i), Figure S8 in the Supporting Information). [17] The reaction rates were plotted against their a-c H BDE in Figure 2 (i). With ethylbenzene as the solvent, the reaction rate decreased with the increase of a-c H BDE of the alcohols. This suggested the alcohol oxidation process is closely related to a- C H bond activation. A phenomenon that should be noticed is that the C H BDE in ethylbenzene is 87 kcal mol 1, whereas for some alcohols, such as cyclohexanol (92.8 kcal mol 1 ), the a-c H BDE exceeds this value, which suggested this process could not only activate C H bonds weaker than the hydrocarbon solvent but also active those alcohols with a C H bond stronger than the hydrocarbon solvent. This is thus a new route to activate the C H bond through first activating a relative weak C H bond to generate free radicals and then activate a relatively strong C H bond. The effect of solvent Figure 3. Alcohol oxidation by different solvents. [a] With tert-butyl hydroperoxide (TBHP) added. Figure 2. i) Reaction rates of different alcohols with ethylbenzene solvent. ii) Reaction rates of p-methylbenzyl alcohol with different hydrocarbon solvents. Reaction conditions: 1 mmol substrate, 50 mg catalyst, 10 ml solvent, 1.0 MPa O 2, 120 8C. Similar results were obtained with other hydrocarbons as the solvent such as tetralin, o-xylene, and p-diethylbenzene (Figure 3). When non-hydrocarbon solvents including methanol, acetonitrile, and dichloromethane were used, the alcohol was not converted. This indicated that the hydrocarbon solvent plays an important role in this process. Moreover, the hydrocarbon solvents themselves were oxidized into the corresponding ketones and alcohols to some extent. The non-hydrocarbon solvent stayed stable during oxidation process. In addition, when an inert hydrocarbon such as toluene or cyclohexane was employed in the reaction, the p-methylbenzyl alcohol could not be oxidized under the same conditions (Figure 3). The above results indicated that solvent oxidation affected the alcohol oxidation process. It was well acknowledged that a free radical mechanism is usually involved in the selective oxidation of hydrocarbon, indicating that the formation of hydrocarbon free radicals is a key factor for the alcohol oxidation. The C H bond in toluene and cyclohexane are too inert to be activated to carbon radicals under the above conditions, and thus the alcohol could not be converted. When a radical initiator was added in toluene solvent, p-methylbenzyl alcohol was converted to p-methylbenzoic acid with 98 % conversion (Figure 3). In addition, the product distribution varied with the type of hydrocarbon, p-methylbenzoic acid was the only product in ethylbenzene and p-diethylbenzene solvent, whereas 36% and 19% of p-tolualdehyde was formed in tetrahydronaphthalene and o-xylene solvent, respectively. This indicated the reactivity of the hydrocarbon free radical affects the alcohol oxidation process. Chem. Asian J. 2017, 00, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim && These are not the final page numbers! ÞÞ

4 The effect of the C H BDE of hydrocarbon solvent A series of hydrocarbons with different C H bond energies were applied as the solvents (Figure 2 ii, Figure S9 in the Supporting Information). [18] A negative correlation between the alcohol reaction rate and the C H BDE of the hydrocarbon solvents was observed. This tendency showed that the oxidation rate of the hydrocarbon could affect the alcohol oxidation rate, meaning these two steps are highly related. Owing to the difference in the C H BDE of the solvent, the types and the generation rates of the free radicals are different for a certain catalyst. The final alcohol oxidation is related to the types and the generation rates of the free radicals. For the hydrocarbon solvents with high C H BDE, although the free radicals generated may have a higher ability to activate alcohols, they can be difficult to activate, thus resulting in a low generation rate. The generation rate played the leading role in the resulting negative correlation in Figure 2 (ii). The effect of peroxide The peroxide formed in situ during the hydrocarbon oxidation may oxidize the alcohol. An experiment was performed to investigate whether the alcohol was oxidized by the in situ formed peroxide (Figure 4). Without the catalyst, 1-phenyl-ethylhydroperoxide (PEHP) is the major product of self-oxidation of ethylbenzene. After ethylbenzene was mainly converted to PEHP, the catalyst and alcohol were added into the reaction medium, and O 2 was replaced with N 2, to ensure PEHP as the sole potential oxidant. The amount of PEHP decreased immediately after the catalyst was added. However, the alcohol was not converted, even PEHP was completely decomposed. This result demonstrated that the alcohol is not oxidized by the in situ formed peroxide. The investigation of reaction mechanism Figure 5. Hammett plot for the oxidation of substituted benzyl alcohols catalyzed by Co-Pr-15. A series of experiments were performed to investigate the reaction mechanism. With butylated hydroxytoluene (BHT) added into the reaction medium to inhibit the free radical process (Table 1, entries 8, 9), the oxidation of ethylbenzene, p- methylbenzyl alcohol, and p-tolualdehyde were all inhibited, implying both the alcohol and aldehyde oxidation rely on the free radicals. In addition, a linear relationship between log(k X / k H ) and the Brown Okamoto constant s + (Figure 5) was established for the oxidation of substituted benzyl alcohols (X = p- Cl, p-no 2, p-me, and p-ome). The resulting Hammett parameter 1 was only 0.07, suggesting that the reaction was insensitive to substituent effects, which support the free radical process. Hot filtration of catalyst slowed down the reaction rate but did not completely stop the reaction (Figure S10 in the Supporting Information). The results indicated that the generation of radicals is mainly caused by the catalyst and the slow oxidation of alcohols after catalyst filtration was due to the already generated free radicals in the solvent. To study the effect of the free radical on the oxidation of alcohol, reaction rates of alcohol and aldehyde as the reactants were measured individually (Figure 6). The rate of aldehyde is 3.4 times faster than that of the alcohol under the same conditions, meaning the rate-determining step is the oxidation of alcohol to aldehyde. The kinetic isotope effect (KIE) was investigated to determine the bond dissociation in the rate-determining step of alcohol oxidation (Table 2). The k H /k D values for p- CH 3 PhCH 2 OD and p-ch 3 PhCD 2 OD are 1.07 and 6.50, respectively. The large value of k H /k D for p-ch 3 PhCD 2 OD shows first KIE, meaning the a-c H bond cleavage is the rate-determining step. All this evidence proved that the reaction undergoes a free radical process and the activation of a-c H bond of alcohol is the key step. The proposed mechanism Figure 4. Alcohol oxidation by the peroxide. Reaction conditions: 10 ml ethylbenzene, 120 8C, 1.0 MPa O 2 ; at the vertical line, 1 mmol substrate and 50 mg catalyst was added in and O 2 was replaced by N 2. In this catalytic process, all these experiment results showed the alcohol was activated by the free radicals. Based on the experiment results and the references, a proposed mechanism similar with the N-hydroxyphthalimide (NHPI) system was illustrated in Scheme 1. [19] In the presence of the catalyst, the hydrocarbon-based free radicals were generated from the oxidation of hydrocarbon solvent. These radicals could react with alcohols and abstract the a-c H, leading to the formation of al- && Chem. Asian J. 2017, 00, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ÝÝ These are not the final page numbers!

5 Figure 6. Reaction rate of alcohol and aldehyde oxidation with Co-Pr-15. Table 2. Reaction rates and kinetic isotopic effects (KIEs) for aerobic oxidation of p-methylbenzyl alcohol. Entry Reactants Reaction rates [s 1 ] KIE (k H /k D ) Reaction conditions: 10 ml solvent, 1 mmol substrate, 1208C, 50 mg catalyst, 1.0 MPa O 2. cohol radicals. These alcohol free radicals could react with oxygen and thus further converted to the aldehyde, and the aldehyde was finally converted to the acid smoothly. According to this proposed mechanism, the reason behind the hydrophobic effect promoting the alcohol oxidation (see above) could be explained. In this catalytic process, the alcohol oxidation rate is highly related to the generation rate of hydrocarbon free radicals. Under the same conditions, the difference in the alcohol oxidation rate could only be the result of different generation rates of free radicals, meaning the catalysts could influence the alcohol oxidation rate through the control of free radicals generation rate. Previously, a number of literature reports have shown that the oxidation rate of hydrocarbon increases with the hydrophobicity of the catalyst, which suggests a higher generation rate of free radicals. In this catalytic process, the hydrophobic catalyst gave a higher oxidation rate of the hydrocarbon than the hydrophilic one, which finally results in a higher oxidation rate of the alcohols. Conclusion We have reported a highly active hydrophobic cobalt catalyst for alcohol oxidation under the assistance of hydrocarbon solvent with oxygen as the terminal oxidant. In this process, the hydrocarbon solvent not only played the role of the reaction medium, but also supplied free radicals to active the a-c H bond activation of the alcohols. The hydrophobicity of the catalyst favors the generation of hydrocarbon free radicals, thus enhancing the oxidation rate of alcohols. The present work provided a new strategy for alcohol oxidation, which can guide the design on an alcohol oxidation system. Experimental Section Scheme 1. Propose mechanism of the catalysis by the cobalt catalyst under the assistance of hydrocarbon solvent. Catalytic oxidation of alcohol Catalytic reactions were performed in a 50 ml of autoclave reactor with a Teflon insert inside. Typically, 10 ml hydrocarbon was added as the solvent, 1 mmol alcohol and 50 mg of catalyst were placed in the reactor. Then, after being sealed, the reactor was heated to the reaction temperature, while agitation was ensured by using an external magnetic stirrer. Upon heating to the reaction temperature, the reactor was charged with 1.0 MPa of O 2 and O 2 was fed continuously to maintain constant pressure. The reaction was carried out at 393 K for 4 h. Reaction products were identified by using an Agilent 6890N GC/5973 MS detector and quantitated with an internal standard (1,4-dichlorobenzene) method by Agilent 6890D GC equipped with Innovex capillary column (50 m 0.32 mm 0.4 mm). The products were quantified by a double injection: triphenylphosphine (1 m in THF) was added to one of the Chem. Asian J. 2017, 00, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim && These are not the final page numbers! ÞÞ

6 samples to reduce the peroxide product to the alcohol. For the kinetic study, liquid samples (~20 ml) were extracted periodically using the syringe. Typically, 8 15 points were used. Synthesis of the catalyst First, two kinds of solution (solutions A, B) were obtained. Solution A was composed of 15 g of Np-7, 31.5 g of cyclohexane, and 8 g of n-butyl alcohol; solution B was the metal ammonia complex water solution (0.13 g of Co(OAc) 2 4H 2 O, 5.5 g of H 2 O, and 2 g of NH 3 H 2 O (21%)). A microemulsion was obtained by blending solutions A and B. To this microemulsion, 2 g TEOS was added slowly under stirring. After 1 h, the mixture of TEOS and PTMS was added, with the ratio of TEOS and PTMS as 5.6:1. The stirring was continued for 24 h. It was then centrifuged, washed with hot ethanol to remove the surfactant, and dried at 353 K for 12 h. The catalyst was named Co-Pr-15. The other catalysts were synthesized with different ratio of TEOS and PTMS. The catalysts were named Co-Pr-5, Co-Pr-25, Co-Pr-35 with the ratios 19, 3, and The non-organic group containing Co-Pr-0 was synthesized without PTMS. Synthesis of p-ch 3 PhCH 2 OD A 60% suspension of sodium hydride in mineral oil was washed with dry pentane under an argon atmosphere, and the residual solvent was removed under vacuum. Undiluted p-methylbenzyl alcohol was added to the reaction flask slowly, and the resulting suspension was stirred for 1 h at room temperature before being quenched with 2 equiv of D 2 O (99.9 % atom%d). The deuterated alcohol was extracted with dry ether, and the organic layer was dried with sodium sulfate before removing the solvent under vacuum with a mechanical pump to afford the deuterated products. Synthesis of p-ch 3 PhCD 2 OD To a stirred suspension of LiAlD 4 (0.50 g, 12 mmol) in THF (40 ml) at 08C was added a solution of methyl benzoate (3.00 g, 22 mmol) in THF (20 ml). The reaction was stirred at room temperature and was monitored by GC/MS until consumption of the benzoate. The resulting solution was quenched at 08C with D 2 O and was extracted with ethyl acetate (3 20 ml). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Characterizations Fourier transform infrared (FTIR) spectra were collected between 4000 and 400 cm 1 with a Bruker Tensor 27 spectrometer in KBr media. Water contact angles were measured with a contact angle measuring system JC 2000 C1. The nuclear magnetic resonance spectra were recorded with a Bruker DRX-400 spectrometer. ICP was measured with a PerkinElmer ICP-OES 7300DV. TEM images were recorded with a HITACHI HT7700. SEM images were collected with a Tecnai Quanta 200F. UV/Vis spectra were collected with a SHIMADZU UV Acknowledgments This work was supported by the National Natural Science Foundation of China (Grant nos and ) and the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB ). Conflict of interest The authors declare no conflict of interest. Keywords: alcohol cobalt hydrocarbon solvent hydrophobic oxidation [1] Z. Guo, B. Liu, Q. H. Zhang, W. P. Deng, Y. Wang, Y. H. Yang, Chem. Soc. Rev. 2014, 43, [2] S. E. Davis, M. S. Ide, R. J. Davis, Green Chem. 2013, 15, [3] a) A. E. Shilov, G. B. Shul pin, Chem. Rev. 1997, 97, ; b) K. Jähnisch, V. Hessel, H. Lçwe, M. Baerns, Angew. Chem. Int. Ed. 2004, 43, ; Angew. Chem. 2004, 116, ; c) D. E. de Vos, B. F. Sels, P. A. Jacobs, Adv. Catal. 2001, 46, 1 87; d) S. S. Stahl, Angew. Chem. Int. Ed. 2004, 43, ; Angew. Chem. 2004, 116, ; e) T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, ; f) C. L. Hill, Angew. Chem. Int. Ed. 2004, 43, ; Angew. Chem. 2004, 116, ; g) R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, [4] a) Y. He, J. Feng, G. L. Brett, Y. Liu, P. J. Miedziak, J. K. Edwards, D. W. Knight, D. Li, G. J. Hutchings, ChemSusChem 2015, 8, ; b) V. C. Corberµn, M. E. Gonzµlez-PØrez, S. Martínez-Gonzµlez, A. Gómez- AvilØs, Appl. Catal. A 2014, 474, [5] a) M. Wang, F. Wang, J. Ma, C. Chen, S. Shi, J. Xu, Chem. Commun. 2013, 49, ; b) I. Gandarias, P. J. Miedziak, E. Nowicka, M. Douthwaite, D. J. Morgan, G. J. Hutchings, S. H. Taylor, ChemSusChem 2015, 8, ; c) A. Corma, Nat. Mater. 2016, 15, [6] T. Lu, Z. Du, J. Liu, H. Ma, J. Xu, Green Chem. 2013, 15, [7] a) G. Zhang, K. V. Vasudevan, B. L. Scott, S. K. Hanson, J. Am. Chem. Soc. 2013, 135, ; b) K.-i. Shimizu, K. Kon, M. Seto, K. Shimura, H. Yamazaki, J. N. Kondo, Green Chem. 2013, 15, [8] a) D. Obermayer, A. M. Balu, A. A. Romero, W. Goessler, R. Luque, C. O. Kappe, Green Chem. 2013, 15, ; b) H. Song, B. Kang, S. H. Hong, ACS Catal. 2014, 4, [9] a) M. T. Räisänen, A. Al-Hunaiti, E. Atosuo, M. Kemell, M. Leskela, T. Repo, Catal. Sci. Technol. 2014, 4, ; b) H.-Y. Sun, Q. Hua, F.-F. Guo, Z.-Y. Wang, W. X. Huang, Adv. Synth. Catal. 2012, 354, [10] C. Chen, B. Liu, W. Chen, Synthesis 2013, 45, [11] L. Geng, M. Zhang, W. Zhang, M. Jia, W. Yan, G. Liu, Catal. Sci. Technol. 2015, 5, [12] a) Y. Yan, X. Tong, K. Wang, X. Bai, Catal. Commun. 2014, 43, ; b) M. Jafarpour, A. Rezaeifard, V. Yasinzadeh, H. Kargar, RSC Adv. 2015, 5, ; c) J. Yu, Y. Luan, Y. Qi, J. Hou, W. Dong, M. Yang, G. Wang, RSC Adv. 2014, 4, [13] R. V. Jagadeesh, H. Junge, M. M. Pohl, J. Radnik, A. Bruckner, M. Beller, J. Am. Chem. Soc. 2013, 135, [14] L. Wang, F.-S. Xiao, ChemCatChem 2014, 6, [15] L. Wang, H. Wang, F. J. Liu, A. M. Zheng, J. Zhang, Q. Sun, J. P. Lewis, L. F. Zhu, X. J. Meng, F. S. Xiao, ChemSusChem 2014, 7, [16] C. Chen, S. Shi, M. Wang, H. Ma, L. Zhou, J. Xu, J. Mater. Chem. A 2014, 2, [17] a) T. Ishizuka, S. Ohzu, H. Kotani, Y. Shiota, K. Yoshizawa, T. Kojima, Chem. Sci. 2014, 5, ; b) C. Aprile, A. Corma, M. E. Domine, H. Garcia, C. Mitchell, J. Catal. 2009, 264, [18] a) Y.-R. Luo, Comprehensive Handbook of Chemical Bond Energies, 1st ed., CRC, Boca Raton, FL, 2007, 19 96; b) K. Hayashibara, G. H. Kruppa, J. L. Beauchamp, J. Am. Chem. Soc. 1986, 108, ; c) P. DiØvart, H. H. Kim, S. H. Won, Y. G. Ju, F. L. Dryer, S. Dooley, W. J. Wang, M. A. Oehlschlaeger, Fuel 2013, 109, [19] P. J. Figiel, J. M. Sobczak, J. Catal. 2009, 263, Manuscript received: May 12, 2017 Revised manuscript received: June 12, 2017 Accepted manuscript online: June 19, 2017 Version of record online: && &&, 0000 && Chem. Asian J. 2017, 00, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ÝÝ These are not the final page numbers!

7 FULL PAPER Alcohol Oxidation Song Shi, Meng Liu, Li Zhao, Min Wang, Chen Chen,* Jin Gao, Jie Xu* && && Catalytic Oxidation of Alcohol to Carboxylic Acid with a Hydrophobic Cobalt Catalyst in Hydrocarbon Solvent Hydrophobic catalyst: An efficient method for alcohol oxidation was developed through the activation of the a- C H bond by the in situ generated free radicals of hydrocarbon oxidation. A series of catalysts with different water contact angles was applied to investigate the hydrophobic effect of the catalyst. Chem. Asian J. 2017, 00, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim && These are not the final page numbers! ÞÞ

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